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[ CAS No. 98437-24-2 ] {[proInfo.proName]}

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Chemical Structure| 98437-24-2
Chemical Structure| 98437-24-2
Structure of 98437-24-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 98437-24-2 ]

CAS No. :98437-24-2 MDL No. :MFCD00236019
Formula : C8H7BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PKRRNTJIHGOMRC-UHFFFAOYSA-N
M.W : 161.95 Pubchem ID :2776266
Synonyms :

Calculated chemistry of [ 98437-24-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.04
TPSA : 53.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 0.11
Log Po/w (MLOGP) : -0.24
Log Po/w (SILICOS-IT) : -0.23
Consensus Log Po/w : 0.18

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.21 mg/ml ; 0.00747 mol/l
Class : Soluble
Log S (Ali) : -1.98
Solubility : 1.68 mg/ml ; 0.0104 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.17
Solubility : 1.1 mg/ml ; 0.00681 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.89

Safety of [ 98437-24-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 98437-24-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 98437-24-2 ]

[ 98437-24-2 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 98437-24-2 ]
  • [ 210345-56-5 ]
  • [ 224321-54-4 ]
YieldReaction ConditionsOperation in experiment
44% With triethylamine In N,N-dimethyl-formamide at 100℃; for 2.5h;
  • 2
  • [ 98437-24-2 ]
  • [ 1122-91-4 ]
  • [ 53348-90-6 ]
YieldReaction ConditionsOperation in experiment
96% With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 12h; Schlenk technique; Inert atmosphere;
95% With potassium carbonate In xylene at 130℃; for 20h;
86% With triethylamine In ethanol at 140℃; for 0.1h; microwave irradiation;
84% With bis-triphenylphosphine-palladium(II) chloride; triethylamine In ethanol at 140℃; for 0.133333h; Microwave irradiation; Flow reactor;
76% With potassium carbonate; cesium fluoride In N,N-dimethyl acetamide; water at 225℃; microwave irradiation;
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; water; toluene Reflux; General Procedure for the Synthesis of 4-Aryl-substituted benzaldehydes 47b-m. General procedure: Tetrakis(triphenylphosphine)palladium(0) (0.0168 mmol) was added to a solution of 4-bromobenzaldehyde (50, 5.6 mmol) in ethanol-toluene (40 mL, 1:1). After 15 min, the appropriate boronic acid 51b-m (6.75 mmol) was added, followed by sodium hydrogen carbonate (22.4 mmol) and water (11 mL). The resulting mixture was heated under reflux for 9-15 hours. After cooling, the reaction mixture was filtered through Celite, the organic phase was separated, washed with brine (2x20 mL), dried and the solvent evaporated in vacuo. The residue thus obtained was purified by flash-chromatography. Elution by light petroleum-ethyl acetate mixtures afforded the desired compounds.

  • 3
  • [ 98437-24-2 ]
  • [ 928-90-5 ]
  • 5-benzofuran-2-yl-hex-5-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With acetic acid In 1,4-dioxane at 70℃; for 12h;
  • 4
  • [ 924-44-7 ]
  • [ 98437-24-2 ]
  • [ 201230-82-2 ]
  • [ 39959-51-8 ]
  • benzofuran-2-yl-(1-oxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester [ No CAS ]
  • 5
  • [ 98437-24-2 ]
  • [ 76334-36-6 ]
  • [ 730952-29-1 ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 24h; Schlenk technique;
78% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; benzene Heating;
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 70℃; for 12h; Schlenk technique; Inert atmosphere;
  • 6
  • [ 98437-24-2 ]
  • [ 154343-51-8 ]
  • [ 687637-93-0 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane for 19h; Heating;
  • 7
  • [ 98437-24-2 ]
  • [ 19978-41-7 ]
  • 3-benzofuran-2-yl-5-bromo-pyran-2-one [ No CAS ]
  • 8
  • [ 98437-24-2 ]
  • [ 19978-41-7 ]
  • 5-benzofuran-2-yl-3-bromo-pyran-2-one [ No CAS ]
  • 3,5-bis-benzofuran-2-yl-pyran-2-one [ No CAS ]
  • 9
  • [ 98437-24-2 ]
  • [ 409346-90-3 ]
  • 6-(1-benzofuran-2-yl)-3-ethyl-2-methylquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% With tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In 1,4-dioxane for 8h; Heating;
  • 10
  • [ 98437-24-2 ]
  • [ 16357-59-8 ]
  • 2-(2-benzofuranyl)-1-ethoxycarbonyl-1,2-dihydroquinoline [ No CAS ]
  • 11
  • [ 98437-24-2 ]
  • [ 16239-18-2 ]
  • 6-(benzofuran-2-yl)-1-bromonaphthalen-2-ol [ No CAS ]
  • 12
  • [ 98437-24-2 ]
  • [ 32138-69-5 ]
  • 17-(2'-benzofuranyl)androsta-5,16-dien-3β-ol [ No CAS ]
  • 13
  • [ 98437-24-2 ]
  • [ 41014-29-3 ]
YieldReaction ConditionsOperation in experiment
95% With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 5h; General procedure for homocoupling of arylboronicacid General procedure: In a 50 mL round bottomed flask phenylboronic acid (1mmol), DMF (2 ml), catalyst (60 mg), KOH (1 mmol) wereadded and this heterogeneous mixture was vigorously stirredfor the required time at room temperature. After completionof reaction (monitored by TLC), the reaction mixture was filteredto separate the catalyst. The organic product was extractedwith ethyl acetate (3x10 ml). The combined organicfractions were dried over sodium sulphate and concentrated.The residue was purified by silica gel column chromatographywith hexane as eluent to afford the desired product. Theprepared products were characterized by NMR and massspectral analysis.
90% With water at 20℃; for 24h; chemoselective reaction;
71% With air In methanol at 20℃;
36% With Fe3O4 magnetic nanoparticle-supported Cu(II)-β-cyclodextrin complex In N,N-dimethyl-formamide at 25℃; for 4h;
35% With copper(II) sulfate In N,N-dimethyl-formamide at 50℃; for 3h; Molecular sieve;
26% With air; [{(1,10-phenanthroline)Cu(μ-OH)}2Cl2]*3H2O In isopropyl alcohol at 28℃; for 24h;
4% With potassium fluoride; palladium diacetate In water; acetonitrile at 70℃; for 12h; Synthesis of the fluorescent benzofuran dimer Benzofuran-2-boronic acid (70 mg, 0.40 mmol), Pd(OAc)2 (9.0 mg, 0.040 mmol) were dissolved in 2.0 mL of acetonitrile. To this solution, 1.0 mL of KF (20 mg, 0.35 mmol) in water was added and then the mixture solution was heated at 70 °C for 12 h. After cooling to room temperature, 30 mL of 10% HCl aqueous solution were added to the reaction mixture. The layers were separated, and the aqueous layer was extracted three times with 20 mL chloroform. The combined organic layer was concentrated under vacuum. The residue was recrystallized from 0.50 mL of ethyl acetate to give yellow crystals; yield: 2.0 mg, 4.0%.

  • 14
  • [ 98437-24-2 ]
  • [ 1538-62-1 ]
  • [ 1839-72-1 ]
YieldReaction ConditionsOperation in experiment
88% In 1,4-dioxane at 60℃; for 6h;
  • 15
  • [ 98437-24-2 ]
  • [ 35109-88-7 ]
  • (2R,3R,4S,5R)-2-{6-amino-2-(benzofuran-2-yl)-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydrofuran-3,4-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% With caesium carbonate In ethanol; toluene at 120℃; for 0.666667h; Microwave irradiation; 14 Example 14; Preparation of (2R3RAS,5R)-2- {6-amino-2-(benzofuran-2-yl)-9H-purin-9-yl} -5-(hvdroxymethyl)tetrahydrofuran-3 ,4-diol 13; Scheme 13; A solution of 2-iodo adenosine (200mg, 0.51mmol), 2-benzofuranylboronic acid (99mg, O.lmmol), cesium carbonate (364mg, 1.12mmol) and Pd(PPlIs)4 (59mg, 0.051mmol) in toluene (1.2mL) and ethanol (2.4mL) was heated in a Biotage microwave (12O0C, absorption high, pre-stirring 15 s) for 40min. The solvents were then removed in vacuo and the residue dissolved in EtOAc (15mL) and washed with sat. aq. NaHCO3 (15mL x2) and brine (15mL) and dried over MgSO4. Purification by flash column chromatography (normal phase, ICN silica, 2Og, 18-32μ, gradient 0-20% ethanol in DCM, residue dry loaded, product eluted in 15% ethanol) and by reverse phase prep HPLC (Phenomenex Synergi, RP -Hydro 150 x 10mm, lOμ, 2OmL per min, gradient 5-100% acetonitrile in water over lOmin, product eluted in 35% acetonitrile) afforded the title compound 13 as a white solid (4.9mg, 3%).HPLC (Phenomenex Synergi, RP-Hydro, 150 x 4.6mm, 4u, 1.5mL per min, 3O0C, gradient 5-100% acetonitrile (+0.085% TFA) in water (+0.1% TFA) over 7min - held for 30s, 200- 300nm): Retention time 4.13min, 100%.LCMS (Phenomenex Synergi, RP-Hydro, 15O x 4.6mm, 4u, 1.5mL per min, 3O0C, gradient 5-100% acetonitrile (+0.085% TFA) in water (+0.1% TFA) over 7min - held for 30s, 200- 300nm): Retention time 4.61 min, 100%, ES+: 384.469 [MH]+.
  • 17
  • [ 104-92-7 ]
  • [ 98437-24-2 ]
  • [ 19234-04-9 ]
YieldReaction ConditionsOperation in experiment
100% With tri-tert-butyl phosphine; palladium diacetate; potassium hydroxide In tetrahydrofuran; water at 24℃; for 0.0833333h; Flow reactor;
90% With tetra-butylammonium acetate In ethanol at 120℃; for 0.166667h; microwave irradiation;
89% With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 2h; 3. General procedure for Suzuki-Miyaura coupling: General procedure: To a mixture of aryl halide (1 mmol), arylboronic acid (1.2 mmol), Pd-AcAc-Am-Fe3O4/SiO2 (30 mg ), and K2CO3 (3 mmol), DMF: water (8:2, 5 mL) was added and stirred at 80 °C under aerobic conditions. After completion of reaction, monitored by TLC, the reaction mixture was cooled. The catalyst was separated by using external magnet. The product was extracted with ethylacetate (2×10 mL) The organic layer was dried with Na2SO4 and then concentrated on a rotary evaporator afforded corresponding biaryls in excellent yield. The crude products were then purified by column chromatography (2 % ethyl acetate). All synthesized products were confirmed from physical constant IR, 1H and 13C NMR.
88% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h; 2.4. General procedure for Suzuki-Miyaura cross-coupling General procedure: A round bottom flask (50 mL) equipped with condenser was chargedwith aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3(2 mmol), Pd(II)-AMP-CellAl2O3 (40 mg) and dimethyl formamide(DMF) (5 mL). The mixture was stirred in an oil bath at 80 °C. Uponcompletion of the reaction as monitored by thin layer chromatography(TLC) (petroleum ether:ethyl acetate, 95:0.5), the reaction mixture wasfiltered. The filtrate was extracted with ethyl acetate (3 × 5 mL). Thecombined organic layers were collected, dried over anhydrous Na2SO4,and concentrated in vacuum to afford the crude products. These productswere purified by silica gel column chromatography (Ether /EtOAc = 9:1 v/v).
71% With palladium diacetate; potassium carbonate In tetrahydrofuran; water for 13h; Inert atmosphere; Reflux;
63% With potassium carbonate In water at 100℃; for 12h;
62% With potassium carbonate In xylene at 130℃; for 20h;
50% With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 6h; Schlenk technique;
With potassium carbonate In water for 4h; Reflux; 2.3 General procedure for the hetero-coupling of aryl boronic acids with aryl halides General procedure: To a mixture of Pd(II)-β-CD (0.001mol%, based on palladium, 0.23mL from a solution of 1mg in 100mL water, see Table2 for amount of catalyst) in 2mL water was added aryl halide (0.2mmol), arylboronic acid (0.24mmol), and K2CO3 (0.3mmol). The resulting mixture was stirred at reflux for 1-12h (Table2). After cooling, the product was extracted with n-hexane (2×3mL) and dried over Na2SO4. The product was purified by flash chromatography and characterized with 1H and 13CNMR (in CDCl3 and DMSO solvents) to afford biaryls 3a-s in 56-100% yields. All products are known and most of them are commercially available (see supporting information).

  • 18
  • [ 98437-24-2 ]
  • [ 623-00-7 ]
  • [ 41013-94-9 ]
YieldReaction ConditionsOperation in experiment
91% With tetra-butylammonium acetate In ethanol at 120℃; for 0.166667h; microwave irradiation;
90% With potassium carbonate In ethanol; water at 20℃; for 0.5h; Microwave irradiation; 2.3. General procedure for Suzuki reactions Aryl bromide (0.51 mmol, 1 eq.) was dissolved in a mixture of 8 mL H2O:EtOH (1:1) and placed in a 35-mL microwave tube. To this were added the aryl boronic acid (0.61 mmol, 1.2 eq.) and potassium carbonate (1.53 mmol, 3 eq.). Palladium on graphene nanoparticles (Pd/G) (2.1 mg, 1.53 μmol, 0.3 mol%) were then added, and the tube was sealed and heated under microwave irradiation (250 W, 2.45 MHz) at the certain temperature and time which is indicated in Table 2. Upon the completion of the reaction period, the reaction mixture was diluted with 20 mL of H2O and extracted with CH2Cl2 (3 × 50 mL). The organic layers were combined, dried over anhydrous Na2SO4, and filtered. The solvent in the filtrate was then removed in vacuo to give a solid. The pure products were obtained by flash chromatography using hexane:ethyl acetate as the eluent or by washing the solid products with an appropriate non-polar solvent such as hexanes followed by decanting the hexanes layer.
88% With potassium carbonate In xylene at 130℃; for 20h;
  • 19
  • [ 98437-24-2 ]
  • [ 35450-36-3 ]
  • methyl 2-(benzofuran-2-yl)-5-methoxybenzoate [ No CAS ]
  • 20
  • [ 98437-24-2 ]
  • [ 586-78-7 ]
  • [ 787-64-4 ]
YieldReaction ConditionsOperation in experiment
98% With sodium phosphate In water; isopropyl alcohol at 80℃; for 1h;
98% With sodium phosphate dodecahydrate; palladium 10% on activated carbon In water; isopropyl alcohol at 80℃; for 1h; Inert atmosphere;
94% With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 6h; Schlenk technique; Inert atmosphere;
92% With tetra-butylammonium acetate In ethanol microwave irradiation;

  • 21
  • [ 4595-59-9 ]
  • [ 98437-24-2 ]
  • 5-(benzofuran-2-yl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With sodium phosphate dodecahydrate; palladium 10% on activated carbon In isopropyl alcohol at 80℃; for 12h; Inert atmosphere;
95% With sodium phosphate In isopropyl alcohol at 80℃; for 3h;
89% With C43H37ClFeNiP2*C4H8O; potassium carbonate In tetrahydrofuran; acetonitrile at 50℃; for 12h; Inert atmosphere;
72% With tetra-butylammonium acetate In ethanol at 120℃; for 0.166667h; microwave irradiation;

  • 22
  • [ 109-04-6 ]
  • [ 98437-24-2 ]
  • [ 7035-05-4 ]
YieldReaction ConditionsOperation in experiment
99% With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; water monomer; toluene for 12h; Inert atmosphere; Reflux;
92% With tetra-butylammonium acetate In ethanol at 120℃; for 0.166667h; microwave irradiation;
91% With palladium diacetate; anhydrous sodium carbonate In water monomer; propan-2-one at 20℃; for 8h; Inert atmosphere;
91% With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In tetrahydrofuran at 100℃; for 16h; Inert atmosphere;
87% With PdCl<SUB>2</SUB>(PPh<SUB>3</SUB>)<SUB>2</SUB>; potassium carbonate In 1,2-dimethoxyethane; water monomer at 80℃; for 14h;
85% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane at 90℃; for 12h; 8 Synthesis intermediate (524-a): Place 2-bromopyridine (23.41g, 1.2eq) and benzofuran-2-boronic acid (20g, 1eq) in a dry two-neck flask, Pd(PPh3)4 (7.14g, 0.05eq), potassium carbonate (52.36g, 4eq), then 250mL of dioxane was added, and the reaction was stirred at 90°C for 12 hours. Cool to room temperature, spin to dry after the reaction is complete, use dichloromethane and water, dry over magnesium sulfate, and spin to dry. Then, it was separated and purified by a silica gel chromatography column to obtain the solid intermediate (524-a) with a yield of 85%.
With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; water monomer; toluene at 95℃; for 18h;
With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; water monomer; toluene for 18h; Inert atmosphere; Reflux;
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; water monomer; toluene at 100℃; for 18h; Inert atmosphere;

  • 23
  • [ 98437-24-2 ]
  • [ 583-55-1 ]
  • [ 129503-26-0 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 4h; Heating; A-1 Preparation Example A-1. Preparation ofCompound A-1 After benzofuran-2-boronic acid (30 g, 185 mmol)and 1-bromo-2-iodobenzene (53.2 g, 189 mmol) were addedto dioxane (300 ml), a 2M aqueous potassium carbonatesolution (100 ml) was added thereto, tetrakistriphenyl-phosphinopalladium(4.28 g, 2 mol %) was put thereinto, andthen the resulting mixture was heated and stirred for 4 hours.The temperature was lowered to normal temperature, thereaction was terminated, and then the potassium carbonatesolution was removed to separate the layers. After thesolvent was removed, the residue was colunmed withhexane to prepare Compound A-1, which is a colorless oil(42.7 g, 85%). MS[M+Ht=272.98
With tetra-butylammonium acetate In ethanol microwave irradiation;
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 5h; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In dimethyl sulfoxide at 80℃; for 5h; Inert atmosphere; Schlenk technique;

  • 24
  • [ 105994-77-2 ]
  • [ 98437-24-2 ]
  • 4-benzofuran-2-yl-1-methyl-5-phenyl-1H-pyrazole [ No CAS ]
  • 25
  • [ 98437-24-2 ]
  • [ 99-90-1 ]
  • [ 132932-61-7 ]
YieldReaction ConditionsOperation in experiment
97% With tetra-butylammonium acetate In ethanol microwave irradiation;
93% With tripotassium phosphate tribasic; (bdppmapy)PdCl<SUB>2</SUB> In ethanol; N,N-dimethyl-formamide at 78℃; for 1.5h; Inert atmosphere; Schlenk technique; 3 General procedure for the Suzuki-Miyaura reaction General procedure: The ligand bdppmapy (4.9mg, 0.01mmol) and PdCl2 (1.8mg, 0.01mmol) were added to a Schlenk tube containing a magnetic stirrer bar, and then degassed DMF (1mL) was added. The mixture was stirred 3h at room temperature. 4′-Bromoacetophenone (199mg, 1mmol), 4-methoxyphenylboronic acid (228mg, 1.5mmol), and K3PO4 (637mg, 3mmol) were added to another Schlenk tube with a magnetic stirrer bar. The dissolved mixture of bdppmapy/PdCl2 (2μL, 0.00002mmol) was transferred to the Schlenk tube of reactants by syringe. Then, ethanol (4mL) was added. The reaction mixture was heated at reflux for 1.5h. At the end of the reaction, the solution was cooled to room temperature and water (5mL) was added. The mixture solution was extracted with ethyl acetate (3×5mL) and the organic layer was dried over magnesium sulfate. The dried solution was filtered and reduced to approx. 1-2mL under vacuum, then purified with silica gel chromatography to give the corresponding product with an isolated yield.
93% With tripotassium phosphate tribasic; (bdppmapy)PdCl<SUB>2</SUB> In ethanol for 1.5h; Inert atmosphere; Reflux; 23 A palladium-phosphine compound was used to catalyze the reaction of 4-bromoacetophenone and benzofuran-2-boronic acid 4-Bromoacetophenone (1 mmol), benzofuran-2-boronic acid (1.5 mmol) and K were added3PO4(3 mmol), and the catalyst obtained in Example 1 (100 μL, 0.001 mmol) were added to a dry reaction tube with a magnetic stir bar, and then absolute ethanol (4 mL) was added.The reaction tube was then treated with N.2Displacement 3 times, reflux, stirring reaction 1.5 h.After the reaction, the solution was cooled to room temperature, 5 mL of water was added and the mixture was extracted with 3 x 5 mL of ethyl acetate. The organic phases were combined and the organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated by rotary evaporation. Chromatography separated to give the desired product (93% yield) and characterized by nuclear magnetic resonance.
90% With C42H48Cl4N4Pd2S2; potassium carbonate In water monomer at 60℃; for 5h; Inert atmosphere;
83% With sodium salt of phosphorous acid In water monomer; isopropanol at 80℃; for 2h;
83% With sodium phosphate tribasic dodecahydrate; palladium 10% on activated carbon In water monomer; isopropanol at 80℃; for 2h; Inert atmosphere;
66% With potassium carbonate In xylene at 130℃; for 20h;
65% With tripotassium phosphate tribasic; tris-(dibenzylideneacetone)dipalladium(0); 5-(dicyclohexylphosphanyl)-1-(2,6-dimethoxyphenyl)-1H-1,2,3-triazole In acetonitrile at 100℃; for 1h; Inert atmosphere; Microwave irradiation;
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,2-dimethoxyethane at 90℃; Inert atmosphere;

  • 26
  • 2-[(4-iodo-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester [ No CAS ]
  • [ 98437-24-2 ]
  • 2-[(4-benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With sodium carbonate In 1,2-dimethoxyethane; water at 65℃; for 2h; 2.III Step III; 2-[(4-Benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester Step III 2-[(4-Benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester To a degassed solution of 2-[(4-Iodo-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester (40 mg, 0.068 mmol) and benzofuran-2-boronic acid (20 mg, 0.124 mmol) in a mixture of DME (3 ML) and 2M aqueous Na2CO3 (1.5 ML), Pd(PPh3)4 (4 mg) was added and the reaction mixture was stirred at 65° C. for 2 h under a N2 atmosphere.The reaction mixture was diluted with ethyl acetate and water.The organic layer was separated, dried (Na2SO4), concentrated.The residue was purified by column chromatography using ethyl acetate and hexane (1:9) to obtain 2-[(4-Benzofuran-2-yl-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester (39 mg, 100%) as a thick syrup. 1H NMR (af-2783) (CDCl3, 400 MHz): δ7.2 (d, 2H), 7.62 (d, 1H), 7.55 (d, 1H), 7.30-7.15 (m, 7H), 7.12 (d, 2H), 6.96 (s, 1H), 6.51 (s, 1H), 4.72 (m, 3H), 3.80, 3.40 (2s, 6H), 3.28 (dd, 1H), 3.02 (dd, 1H), 2.71, 2.58, 2.12 (3s, 9H).
  • 27
  • [ 98437-24-2 ]
  • [ 111-85-3 ]
  • [ 39195-68-1 ]
YieldReaction ConditionsOperation in experiment
74% With potassium phosphate In N,N-dimethyl acetamide at 80℃; for 9h; 7 Examples 2 to 13 Examples 2 to 13 The process of Example 1 was repeated in a similar manner except that 0.4 mmol of each of the boron compounds as shown in Table 1 was used in place of p-methoxyphenylboronic acid and 0.30 mmol of each organic halide as shown in Table 1 was used in place of 1-bromooctane and reaction was conducted for the noted period of time in Table 1.
  • 28
  • [ 98437-24-2 ]
  • [ 111-83-1 ]
  • [ 39195-68-1 ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate In N,N-dimethyl acetamide at 80℃; for 2h; 8 Examples 2 to 13 Examples 2 to 13 The process of Example 1 was repeated in a similar manner except that 0.4 mmol of each of the boron compounds as shown in Table 1 was used in place of p-methoxyphenylboronic acid and 0.30 mmol of each organic halide as shown in Table 1 was used in place of 1-bromooctane and reaction was conducted for the noted period of time in Table 1.
  • 29
  • [ 1701-22-0 ]
  • [ 98437-24-2 ]
  • [ 849222-16-8 ]
YieldReaction ConditionsOperation in experiment
68% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; at 20 - 65℃; for 18.5h;Neat (no solvent); Example 1: Synthesis of 6- (1-BENZOFURAN-2-YL)-2- (TRIFLUOROMETHYL) QUINOLIN-4- yl LH-TETRAAZOL-5-YLMETHYL ether [0099] Step 1: Synthesis of 6- (L-BENZOFURAN-2-YL)-4-HYDROXY-2- (trifluoromethyl) quinoline:; To a flask with <strong>[1701-22-0]6-bromo-4-hydroxy-2-trifluoromethyl-quinoline</strong> (1.00 g, 3.42 mmol) was added K2CO3 (8.55 ML, 1.0 M in H2O, 8.55 mmol) followed by dioxane (85.5 mL). Benzofuran-2-boronic acid (0.665 g, 4.10 mmol) was then added followed by PDCL2 (DPPF) (0. 028 g, 0.0342 mmol). The reaction mixture was stirred at room temperature for 0.5 hour and then heated to 65 C for 18 hours. After concentration, the reaction was diluted with EtOAc (200 ML). The organic layer was washed with 1 N HCL, (20 ML), sat. aq. NAHCO3 (20 mL), and brine (20 mL) and then dried (MGS04). After concentration, the residue was recrystallized from EtOAc to afford the product (0.770 g, 68%) as a solid. Mass spectrum (+ESI, [M+H] +) MLZ 330. 1H NMR (500 MHz, DMSO-d6) : 8 8.68 (s, 1H), 8.37 (d, 1H, J = 9.3 Hz), 8.07 (d, 1H, J = 9.3 Hz), 7.65-7. 75 (m, 3H), 7.38 (t, 1H, J = 7. 7 HZ), 7.30 (t, 1H, J = 7. 7 Hz), and 7.06 ppm (s, 1H).
  • 30
  • [ 98437-24-2 ]
  • [ 159217-89-7 ]
  • [ 239088-84-7 ]
YieldReaction ConditionsOperation in experiment
43% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 3h; Suzuki-type coupling [OF A BORONIC] acid and an aryl halide. A degassed [SUSPENSION OF THE BORONIC ACID (1. 1 EQUIV. ), PDCL2 (PPH3) 2 (0.05 EQUIV. ), AND NA2C03 (5] equiv. ) in [DMF/H2O] (2: 1) was treated at RT under N2 with a degassed (N2) solution of the aryl halide (1.0 equiv. ) in DMF (1/4 of total volume). The mixture was heated to [80XB0;C] for 3hr (the reaction was followed by TLC and worked up after complete consumption of the starting material), cooled to RT, diluted with AcOEt, and washed with H20 (2x). The organic layer was dried (MgSO4) and evaporated. The crude product was purified by flash chromatography to give the product as a solid.; [CORNPOURAD 4.] Coupling of compounds 1 (679 mg, 4.19 mmol) and 3 (1.21 g, 3.79 mmol) according to procedure A gave compound 4 (0.50 g, 43%, white [POWDER, LH-NMR).]
  • 31
  • [ 72287-26-4 ]
  • potassium phosphate [ No CAS ]
  • [ 395101-69-6 ]
  • [ 98437-24-2 ]
  • [ 395101-94-7 ]
YieldReaction ConditionsOperation in experiment
62% In dimethylethylene glycol ether; dichloromethane; A. 3-benzo[b]Furan-2-yl-1-Perhydro-2H-Pyran-2-Yl-1H-Indazole-5-Carbonitrile To a flask containing 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (400 mg, 1.30 mmol) in dimethyl glycol ether (15 mL) was added potassium phosphate (2.75 g), [1,1'-bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with dichloromethane (1:1) (106 mg, 0.130 mmol), and benzo[b]furan-2-boronic acid (315 mg, 1.95 mmol). The reaction mixture was brought to 90° C. under nitrogen conditions for 18 hours. The mixture was condensed and extracted with water (25 mL) and ethyl acetate. The extracts were dried over sodium sulfate, filtered and concentrated. The residue was then purified by chromatography (SiO2, 20percent ethyl acetate/hexanes) to afford the title compound (278 mg, 62percent). ES-MS (m/z) 344[M+1]+.
62% In dimethylethylene glycol ether; dichloromethane; A. 3-benzo[b]furan-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile To a flask containing 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (400 mg, 1.30 mmol) in dimethyl glycol ether (15 mL) was added potassium phosphate (2.75 g), [1,1'-bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with dichloromethane (1:1) (106 mg, 0.130 mmol), and benzo[b]furan-2-boronic acid (315 mg, 1.95 mmol). The reaction mixture was brought to 90° C. under nitrogen conditions for 18 hours. The mixture was condensed and extracted with water (25 mL) and ethyl acetate. The extracts were dried over sodium sulfate, filtered and concentrated. The residue was then purified by chromatography (SiO2, 20percent ethyl acetate/hexanes) to afford the title compound (278 mg, 62percent). ES-MS (m/z) 344[M+1]+.
  • 32
  • [ 35853-45-3 ]
  • [ 98437-24-2 ]
  • [ 260972-85-8 ]
YieldReaction ConditionsOperation in experiment
64% tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; Example 92 4-(2-Benzofuranyl)-2,8-bis(trifluoromethyl)quinoline A solution of <strong>[35853-45-3]4-bromo-2,8-bis(trifluoromethyl)quinoline</strong> (500 mg, 1.45 mmol) in dry dimethoxyethane (10 mL) was treated with tetrakis(triphenylphosphine)palladium (2.3 mg, 10 mol %), stirred for 10 min, treated with benzofuran-2-boronic acid (235 mg, 1.45 mmol) and 2-M Na2CO3 solution (1.45 mL, 2.9 mmol) then refluxed for 2 h. The mixture was cooled, treated with water (10 mL), extracted with EtOAc (3*20 mL), the organic phase was washed with brine (20 mL), dried (MgSO4), concentrated in vacuo and the resulting yellow solid recrystallized from heptane to give the title compound (351 mg, 64%) as an off-white crystalline solid: mp 129-130 C.; IR numax (Nujol)/cm-1 2924, 1592, 1463, 1314, 1145, 1116, 1010, 749 and 691; NMR deltaH (400 MHz, CDCl3) 7.35 (1H, t, J 7.1 Hz), 7.42-7.47 (2H, m), 7.65 (1H, d, J 7.5 Hz), 7.73 (1H, d, J 8.0 Hz), 7.80 (1H, t, J 7.9 Hz), 8.19-8.23 (2H, m) and 8.86 (1H, d, J 9.0 Hz).
  • 33
  • [ 863783-73-7 ]
  • [ 98437-24-2 ]
  • 3-(7-Benzofuran-2-yl-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In water; N,N-dimethyl-formamide at 70℃; for 7h; 173 N,N-Dimethylformamide (1 ml) and a 2 M aqueous potassium carbonate solution (0.5 ml) were added to 3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (compound 14) (30 mg), tetrakistriphenylphosphine palladium (9 mg), and benzo[b]furan-2-boric acid (36 mg) under an argon atmosphere, and the mixture was stirred at 70°C for 7 hr. The reaction mixture was cooled to room temperature, water was added to the cooled mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then extracted with 1 N hydrochloric acid, and the aqueous layer was washed with ethyl acetate. The aqueous layer was rendered alkaline by the addition of potassium carbonate and was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a hexane-acetone system to give the title compound (26 mg, yield 78%). 1H-NMR (CDCl3, 400 MHz): δ 2.40 (s, 3H), 2.67 (s, 3H), 6.43 (d, J = 5.1 Hz, 1H), 7.09 (ddd, J = 7.6, 4.9, 1.2 Hz, 1H), 7.23 - 7.29 (m, 2H), 7.33 (ddd, J = 8.3, 8.3, 1.4 Hz, 1H), 7.40 (s, 1H), 7.55 - 7.61 (m, 2H), 7.64 (d, J = 7.6 Hz, 1H), 7.84 (ddd, J = 7.8, 1.2, 1.2 Hz, 1H), 8.03 (dd, J = 8.8, 1.7 Hz, 1H), 8.41 (d, J = 8.8 Hz, 1H), 8.46 - 8.51 (m, 1H), 8.54 (d, J = 1.4 Hz, 1H), 8.59 (d, J = 5.1 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 444 (M+1)+
  • 34
  • [ 4926-28-7 ]
  • [ 98437-24-2 ]
  • [ 916433-90-4 ]
YieldReaction ConditionsOperation in experiment
67% With caesium carbonate In 1,4-dioxane at 20℃; for 12h; 10 Example 10 Example 10 This example illustrates the formation of 2-benzofuran-2-yl-4-methyl-pyridine. 16.0 g (0.0988 mol) of 2-benzofuranboronic acid, 13.0 g (0.0756 mol) of 2-bromo-4-methyl-pyridine, 18.00 g (0.0553 mol) of cesium carbonate, 0.90 g (0.000983 mol) of tris(dibenzylideneacetone) dipalladium (0), 0.56 g (0.00237 mol) of benzyl-di-tert-butyl-phosphine and 100 ml of dioxane were stirred at room temperature for 12 hours. The reaction mixture was filtered and the solvent was removed under vacuum. The resulting mixture was purified by chromatography on silica gel with eluent petroleum ether/ethyl ether at 10/2.0. Yield of 2-benzofuran-2-yl-4-methyl-pyridine was 10.61 g (67%) as colorless solid with m.p. 92.72° C. 1H NMR (CDCl3) 2.12 (s, 3H, Me) 5.95-8.55 (m, 8H, arom-H). Anal. Calcd. for C14H11NO: C, 80.36; H, 5.30; N, 6.69. Found: C, 80.23; H, 5.19; N, 6.79. The structure has been confirmed by X-ray analysis.
  • 35
  • [ 19755-53-4 ]
  • [ 98437-24-2 ]
  • [ 917966-87-1 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 16h; Example 15; 1-(2-(benzofuran-2-yl)pyridine-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea; 15a. 2-(benzofuran-2-yl)-3-nitropyridine; To a solution of <strong>[19755-53-4]2-bromo-3-nitropyridine</strong> (75 mg, 0.371 mmol) in DME (3 mL) was added benzofuran boronic acid (130 mg, 0.802 mmol), followed by Pd(PPh3)4 (35 mg, 0.03 mmol) and K2CO3 (145 mg, 1.05 mmol). The reaction mixture was stirred at 80 C. for 16 h. The mixture was filtered and washed with CH2Cl2 (10 mL). The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 60% EtOAc in hexane over 30 min as eluting gradient to afford 15a (62 mg, 70%) as a yellowish powder. MS (ES) m/z 241 [M+H]+.
  • 36
  • [ 19755-53-4 ]
  • [ 98437-24-2 ]
  • [ 917966-89-3 ]
YieldReaction ConditionsOperation in experiment
40% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 16h; Example 16; 1-(2-(benzo[b]thiophen-2-yl)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea; 16a. 2-(benzo[b]thiophen-2-yl)-3-nitropyridine; To a solution of <strong>[19755-53-4]2-bromo-3-nitropyridine</strong> (75 mg, 0.371 mmol) in DME (3 mL) was added benzofuran boronic acid (132 mg, 0.802 mmol), followed by Pd(PPh3)4 (35 mg, 0.03 mmol) and K2CO3 (145 mg, 1.05 mmol). The reaction mixture was stirred at 80 C. for 16 h. The mixture was filtered and washed with CH2Cl2 (10 mL). The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 80% EtOAc in hexane over 40 min as eluting gradient to afford 16a (38 mg, 40%) as a yellowish powder. MS (ES) m/z 257 [M+H]+.
  • 37
  • [ 916179-86-7 ]
  • [ 98437-24-2 ]
  • [ 916179-92-5 ]
YieldReaction ConditionsOperation in experiment
77.1% With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 2.5h; 6.i To a degassed solution of 52 (0.200 g, 0.489 mmol) was addedPd(OAc)2 (0.006 g, 0.05 eq.), K2CO3 (0.135 g, 2 eq.) and benzofuran-2-boronic acid EPO 53 (0.103 g, 1.3 eq.) at room temperature (Scheme 10). After degassing and purging with argon (repeated thrice), the reaction mixture was stirred at 9O0C for 2.5 hours. The mixture was allowed to cool to room temperature and diluted with H2O (15 mL). The aqueous solution was extracted with ethyl acetate (5 x 15 mL) and combined organic layer was concentrated under reduced pressure. The residue was purified by flash column chromatography using 20 % ethyl acetate in hexane as solvent system to afford 54 (0.168 g, 77.1 %) as white solid. 1H NMR (CDCl3) 2.34 (s, 3H), 3.97 (s, 3H), 7.11 (s, IH), 7.23-7.27 (m, 3H), 7.31 (t, IH, J=7.3), 7.54 (d, IH, J=8.1), 7.61 (d, IH, J=7.6), 7.84 (d, 2H, J=8.2), 8.09 (2s, 2H), 8.13 (s, IH), 8.65 (s, IH); 13C NMR (CDCl3) 21.64, 51.88, 103.27, 110.71, 113.63, 114.29, 120.95, 123.18, 124.65, 124.88, 126.08, 126.53, 127.05, 127.21, 128.88, 130.21, 134.74, 137.85, 145.76, 149.39, 154.30, 166.38
  • 39
  • [ 5332-24-1 ]
  • [ 98437-24-2 ]
  • [ 1004751-40-9 ]
YieldReaction ConditionsOperation in experiment
100% With sodium phosphate In isopropyl alcohol at 80℃; for 0.5h;
100% With sodium phosphate dodecahydrate; palladium 10% on activated carbon In isopropyl alcohol at 80℃; for 0.5h; Inert atmosphere;
96% With caesium carbonate In N,N-dimethyl acetamide at 80℃; for 13h; Inert atmosphere; chemoselective reaction;
  • 40
  • [ 22200-50-6 ]
  • [ 98437-24-2 ]
  • [ 1062589-66-5 ]
YieldReaction ConditionsOperation in experiment
38% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 90.0h;Heating / reflux; A mixture of Intermediate 5 (0.5 g, 1.73 mmol), benzo[b]furan-2-boronic acid (0.293 g, 1.92 mmol), tetrakistriphenylphosphine palladium catalyst (50 mg) and 2N sodium carbonate (7.78 ml) were heated under reflux in dimethoxyethane (15 ml) for approximately 18 hours. Fresh catalyst (50 mg) was added and heating continued for approximately an addition 72 hours. The solids from the reaction mixture were removed by filtration. The aqueous and organic layers were separated. The organic layer was washed with water and the aqueous washings were back extracted with EtOAc and combined with the organic phases. and al of the organic layers were combined. The combined organic layers were dried using a drying agent such as molecular sieves, filtered, and volatiles removed in vacuo. The resulting residue was chromatographed on silica gel using a gradient eluent of 2-6percent EtOAc/iHexane and the desired product was isolated after combining the appropriate fractions and removing solvent in vauo (18.6 mg, 38percent).
  • 41
  • [ 90145-48-5 ]
  • [ 98437-24-2 ]
  • [ 1054629-45-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 80℃; for 2h; 2-Benzofuranboronic acid (3.1 mmol), <strong>[90145-48-5]5-bromopyridine-2-carboxamide</strong> (3.7 mmol), 2M K2CO3 (aq., 6 mL) and Pd(dppf)Cl2 (0.31 mmol) were mixed and stirred at 80 C. in DMF for 2 h. The reaction mixture was filtered and washed with H2O and EtOAc. DMSO was added to the solid remains and filtered. The filtrate was collected and purified by reverse phase HPLC to afford the title compound as a white solid (2.5 mg). 1H NMR delta ppm 9.18 (d, 1H) 8.46 (dd, 1H) 8.13-8.19 (m, 2H) 7.68-7.78 (m, 4H) 7.43-7.30 (m, 2H); MS m/z 239 (M+H).
  • 42
  • [ 98437-24-2 ]
  • [ 540-37-4 ]
  • [ 782-18-3 ]
YieldReaction ConditionsOperation in experiment
99.5% With sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 125℃; for 2h; 1.003.D STEP D:A mixture of 4-iodo-aniline (25.0 g, 114.1 mmol), 2-benzofuran-boronic acid (27.7 g, 171.2 mmol), PdCl2(O-tolylphosphine) (11.66 g, 14.8 mmol), and Na2CO3(60.49 g, 570.7 mmol) in DME/EtOH/H2O (4:2:l)(700 mL) was heated at 125 °C for 2 h. The reaction mixture was cooled to room temperature, filtered and washed. The solvent was removed under reduced pressure. The residue was partitioned (ethyl acetate/water) and the organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting crude was purified by column chromatography on silica gel, eluting with dichloromcthane to afford 4-benzofuran-2-yl-phenylamine (11) as a pale yellow solid (23.78 g, 99.5%): 1H NMR (300 MHz, CDCl3): δ 7.66 (d, J = 9.0 Hz, 2 H), 7.51 - 7.55 (m, 2 H), 7.20 - 7.23 (m, 2 H), 6.81 (s, 1 H), 6.73 (d, J= 9.0 Hz, 2 H), 3.83 (bs, 2 H) TLC conditions: Uniplate silica gel, 250 microns; mobile phase = ethyl acetate/ hexanes (2: 1); Rf = 0.45.
  • 43
  • [ 49844-90-8 ]
  • [ 98437-24-2 ]
  • [ 1107658-43-4 ]
YieldReaction ConditionsOperation in experiment
43% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 16h; <strong>[49844-90-8]4-Chloro-2-methylthiopyrimidine</strong> (1.6 g, 10.0 mmol), 2-benzofuranboronic acid (1.9 g, 12.0 mmol), tetrakis-(triphenylphosphine)-palladium (0.3 g, 0.3 mmol) were dissolved in dioxane (10 ml) and aqueous Na2CO3 (11 ml, 2M solution in water, 22 mmol) was added. The reaction was heated to 80° C. under argon for 16 h after which time the dioxane was evaporated and the reaction mixture diluted with water and extracted with CH2Cl2. The organic was dried (Na2SO4), concentrated and the residue purified by flash column chromatography (CH2Cl2:n-heptane 8:2) to afford the title compound (1.0 g, 43percent) as a white solid. MS: 243.0 (MH+).
  • 44
  • [ 98437-24-2 ]
  • [ 1107658-93-4 ]
  • [ 1107656-35-8 ]
YieldReaction ConditionsOperation in experiment
73% With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 24h; 14.C (The equivalences of reagents and the yield were calculated for [5-(3-bromo-phenyl)-1-methyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone as starting material.) 0.370 g (0.91 mmol) of the mixture [5-(3-bromo-phenyl)-1-methyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone and [5-(3-benzofuran-2-yl-phenyl)-1-methyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone was dissolved in 8.00 ml of DMF. Then 0.189 g (1.14 mmol, 1.25 eq) of benzo[b]furan-2-boronic acid, 0.360 g (1.64 mmol, 1.80 eq) of K3PO4 and 0.105 g (0.09 mmol, 0.10 eq) of tetrakis-(triphenylphosphine)-palladium were added. The reaction mixture was degassed (argon) several times at each addition. It was heated (100° C.) for 24 h. At RT, the mixture was partitioned between aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous sat. NaHCO3, dried (Na2SO4) and evaporated. Purification by flash chromatography (SiO2, MeOH/CH2Cl2 2:98) gave 0.299 g (73%) of title compound as brown foam. MS: 443.2 (MH+).
  • 45
  • [ 93618-53-2 ]
  • [ 98437-24-2 ]
  • [ 1107658-87-6 ]
YieldReaction ConditionsOperation in experiment
58% With potassium phosphate In water; toluene at 100℃; for 24h; 12.B 1.40 g (4.74 mmol) of 5-(3-bromo-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (6') (and ethyl ester) was dissolved in 15 ml of toluene and 1.6 ml of H2O. Then 1.54 g (9.49 mmol) of benzo[b]furan-2-boronic acid, 5.42 g (25.52 mmol) of K3PO4, 0.29 g (1.04 mmol) of tricyclohexylphosphine and 0.117 g (0.52 mmol) of palladium-II-acetate were added. The reaction mixture was degassed (argon) several times at each addition. The reaction was heated (100° C.) for 24 h. At RT, the mixture was partitioned between chilled water/EtOAc (3×). The organic phases were washed with water, with aqueous sat. NaHCO3, dried (Na2SO4), filtered (black palladium complex stayed with Na2SO4) and evaporated. Then the residual product was dissolved in hot CH2Cl2 and crystallized at RT. It was filtered to give 0.918 g (58%) of 5-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester as white powder. MS: 332.2 (M+).
  • 46
  • [ 98437-24-2 ]
  • [ 13389-03-2 ]
  • [ 1061729-73-4 ]
YieldReaction ConditionsOperation in experiment
81% With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate In water; acetonitrile at 80℃;
80% With [Pd(succinimidate)2(1,3,5-triaza-7-phosphaadamantane)2]; triethylamine In water at 80℃; for 0.166667h; Microwave irradiation; Inert atmosphere;
  • 47
  • [ 98437-24-2 ]
  • [ 1105510-31-3 ]
  • [ 1105510-81-3 ]
YieldReaction ConditionsOperation in experiment
63% With sodium carbonate In water; acetonitrile at 85℃; for 12h; 72 To a stirred and degassed solution of 5-bromo-2-[(2i?,61S)-2,6-dimethylmorpholin-4-yl]pyridine- 3 -carbaldehyde (Intermediate 24, 250 mg, 0.83 mmol) in acetonitrile: water (4:1) mixture(10 mL), was added sodium carbonate (65mg, 0.61 mmol), benzofuran-2-boronic acid (153 mg, 0.91 mmol), 2-dicyclohexylphosphino 2'4'6'-triisopropylbiphenyl (X-phos) (88 mg, 0.18 mmol) and tris(dibenzylideneacetone) dipalladium(O) (56 mg, 0.061 mmol), sequentially and the reaction mixture was heated to 85 0C for 12 hours. The reaction mixture was cooled to room temperature and concentrated. The residue thus obtained was purified over silica gel column using a gradient of ethyl acetate in pet. ether to give product as yellow solid. Yield: 169 mg (63 %). MS (ES) MH+: 337.2 for C20H20N2O3.
  • 48
  • [ 98437-24-2 ]
  • [ 1154058-76-0 ]
  • [ 1154059-19-4 ]
YieldReaction ConditionsOperation in experiment
41% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 1h; Microwave; 45 4-Bromo-3-methyl-N-(2-sulfamoylphenyl)sulfonyl-benzamide (198 mg, 0.46 mmol), benzofuran-2-ylboronic acid (111 mg, 0.69 mmol) and (1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (18.80 mg, 0.02 mmol) were dissolved in N,N-dimethylformamide (2.5 mL) (solvent was bubbled with argon). To this was added 2 M aqueous sodium carbonate (0.685 mL) and the resulting mixture was heated to 120° C. for 1 hour in a microwave. The reaction mixture was filtered through a pad of celite which was rinsed with ethyl acetate. The filtrate was concentrated in vacuo. The residue was dissolved in dimethyl sulfoxide (1.5 mL) and purified by preparative HPLC to give 89 mg (41% yield) of the title compound.1H NMR (400 MHz, DMSO-d6) δ ppm 8.16 (d, 1H), 8.01 (d, 1H), 7.80-7.90 (m, 3H) 7.55-7.73 (m, 4H), 7.23-7.38 (m, 3H), 2.57 (s, 3H), 1.89 (s, 2H); MS (ESI) m/z 471 [M+H]+
41% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 1h; Microwave irradition; 45 4-Bromo-3-methyl-N-(2-sulfamoylphenyl)sulfonyl-benzamide (198 mg, 0.46 mmol), benzofuran-2-ylboronic acid (111 mg, 0.69 mmol) and (1,1'- bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (18.80 mg, 0.02 mmol) were dissolved in N,N-dimethylformamide (2.5 mL) (solvent was bubbled with argon). To this was added 2 M aqueous sodium carbonate (0.685 mL) and the resulting mixture was heated to 120 0C for 1 hour in a microwave. The reaction mixture was filtered through a pad of celite which was rinsed with ethyl acetate. The filtrate was concentrated in vacuo. The residue was dissolved in dimethyl sulfoxide (1.5 mL) and purified by preparative HPLC to give 89 mg (41% yield) of the title compound.1H NMR (400 MHz, DMSO-J6) δ ppm 8.16 (d, 1 H), 8.01 (d, 1 H), 7.80 - 7.90 (m, 3 H), 7.55 - 7.73 (m, 4 H), 7.23 - 7.38 (m, 3 H), 2.57 (s, 3 H), 1.89 (s, 2 H); MS (ESI) m/z All [M+H]+
  • 49
  • [ 98437-24-2 ]
  • [ 1154058-79-3 ]
  • [ 1154059-67-2 ]
YieldReaction ConditionsOperation in experiment
39% With potassium carbonate In tetrahydrofuran; water at 150℃; for 1h; Microwave; 83 4-Bromo-2-fluoro-N-(2-sulfamoylphenylsulfonyl)benzamide (200 mg, 0.46 mmol), benzofuran-2-ylboronic acid (81 mg, 0.50 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (37 mg, 0.05 mmol) and potassium carbonate (379 mg, 2.74 mmol) were dissolved in tetrahydrofuran (5 mL) and water (1 mL) in a microwave vial. The reaction was heated at 150° C. for 60 min in a microwave, filtered through a plug of celite and concentrated in vacuo. Purification by preparative HPLC gave 84 mg (39% yield) of the title compound.1H NMR (DMSO-d6) δ ppm 7.29 (t, 1H) 7.39-7.34 (m, 1H) 7.46 (s, 2H) 7.61 (s, 1H) 7.65 (d, 1H) 7.76-7.67 (m, 9H) 7.85 (t, 1H) 8.07 (d, 1H) 8.23 (d, 1H); MS (ESI) m/z 473 [M-1]-
39% With potassium carbonate In tetrahydrofuran; water at 160℃; for 1h; Microwave irradiation; 83 4-Bromo-2-fluoro-N-(2-sulfamoylphenylsulfonyl)benzamide (200mg, 0.46 mmol), benzofuran-2-ylboronic acid (81 mg, 0.50 mmol), [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium (37 mg, 0.05 mmol) and potassium carbonate (379 mg, 2.74 mmol) were dissolved in tetrahydrofuran (5 mL) and water (1 mL) in a microwave vial. The reaction was heated at 150 0C for 60 min in a microwave, filtered through a plug of celite and concentrated in vacuo. Purification by preparative HPLC gave 84 mg (39% yield) of the title compound.1H NMR (DMSO-J6) δ ppm 7.29 (t, 1 H) 7.39 - 7.34 (m, 1 H) 7.46 (s, 2 H) 7.61 (s, 1 H) 7.65 (d, 1 H) 7.76 - 7.67 (m, 9 H) 7.85 (t, 1 H) 8.07 (d, 1 H) 8.23 (d, 1 H); MS (ESI) m/z 473 [M-I]"
  • 50
  • [ 98437-24-2 ]
  • [ 1154060-47-5 ]
  • [ 1154058-56-6 ]
YieldReaction ConditionsOperation in experiment
24% With sodium carbonate In water; N,N-dimethyl-formamide at 90℃; 1 5-Bromo-N-(2-sulfamoylphenyl)sulfonyl-pyridine-2-carboxamide (57 mg, 0.14 mmol) was dissolved in DMF (800 μl), then benzofuran-2-boronic acid (24 mg, 0.15 mmol) was added followed by the addition of 2M sodium carbonate solution (400 μl). The mixture was subjected to vacuum/argon (×3); tetrakis(triphenylphosphine)palladium (8 mg, 0.05 mol %) was added and the reaction was allowed to stir at 90° C. overnight. Water was added to the cooled mixture that was then acidified (HCl). The resulting solid was filtered off, washed with water and was then purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound as a solid (15 mg, 24% yield).1H NMR (400 MHz, MeOH) δ ppm 9.08 (d, 1H), 8.38 (dd, 1H), 8.33 (dd, 1H), 8.17-8.24 (m, 2H), 7.62-7.74 (m, 3H), 7.58 (d, 1H), 7.44 (s, 1H), 7.31-7.39 (m, 1 ), 7.27 (t, 1H).MS m/z M-H 455.7, M+H 457.7.
24% With sodium carbonate In water; N,N-dimethyl-formamide at 90℃; 1 5-Bromo-N-(2-sulfamoylphenyl)sulfonyl-pyridine-2-carboxamide (57 mg, 0.14 mmol) was dissolved in DMF (800 μl), then benzofuran-2-boronic acid (24 mg, 0.15 mmol) was added followed by the addition of 2M sodium carbonate solution (400 μl). The mixture was subjected to vacuum / argon (x 3); tetrakis(triphenylphosphine)palladium (8 mg, 0.05 mol %) was added and the reaction was allowed to stir at 90 0C overnight. Water was added to the cooled mixture that was then acidified (HCl). The resulting solid was filtered off, washed with water and was then purified by preparative HPLC (XTerra MS C8 column, acetonitrile / ammonium acetate buffer) to give the title compound as a solid (15 mg, 24% yield).1H NMR (400 MHz, MeOH) D ppm 9.08 (d, 1 H), 8.38 (dd, 1 H), 8.33 (dd, 1 H), 8.17 - 8.24 (m, 2 H), 7.62 - 7.74 (m, 3 H), 7.58 (d, 1 H), 7.44 (s, 1 H), 7.31 - 7.39 (m, 1 H), 7.27 (t, 1 H). MS m/z M-H 455.7, M+H 457.7.
  • 51
  • [ 98437-24-2 ]
  • [ 1154060-73-7 ]
  • [ 1154059-64-9 ]
YieldReaction ConditionsOperation in experiment
27% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.5h; Microwave; 80 A mixture of 4-bromo-3-cyano-N-(2-sulfamoylphenylsulfonyl)benzamide (0.24 g, 0.54 mmol), 2-benzofuranboronic acid (0.11 g, 0.70 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium dichloride (0.044 g, 0.050 mmol), N,N-dimethylformamide (4 mL) and 2 M sodium carbonate (0.81 mL, 1.62 mmol) under an atmosphere of argon was heated at 120° C. for 0.5 hour in a microwave. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and evaporated. Purification by preparative HPLC gave 0.071 g (27% yield) of the title compound.1H NMR (DMSO-d6) δ ppm 8.31 (br. s., 1H) 8.16-8.21 (m, 1H) 8.09-8.13 (m, 1H) 8.05-8.08 (m, 1H) 7.96-8.00 (m, 1H) 7.66-7.74 (m, 4H) 7.55-7.59 (m, 1H) 7.29-7.39 (m, 3H) 7.19-7.24 (m, 1H); MS (ESI) m/z 480 [M-1]-.
27% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.5h; Microwave irradition; 80 A mixture of 4-bromo-3-cyano-N-(2-sulfamoylphenylsulfonyl)benzamide (0.24 g, 0.54 mmol), 2-benzofuranboronic acid (0.11 g, 0.70 mmol), 1,1'- bis(diphenylphosphino)ferrocene-palladium dichloride (0.044 g, 0.050 mmol), N, N- dimethylformamide (4 mL) and 2 M sodium carbonate (0.81 mL, 1.62 mmol) under an atmosphere of argon was heated at 120 0C for 0.5 hour in a microwave. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phse was dried over magnesium sulfate and evaporated. Purification by preparative HPLC gave 0.07 Ig (27% yield) of the title compound.1H NMR (DMSO-J6) δ ppm 8.31 (br. s., 1 H) 8.16 - 8.21 (m, 1 H) 8.09 - 8.13 (m, 1 H) 8.05 - 8.08 (m, 1 H) 7.96 - 8.00 (m, 1 H) 7.66 - 7.74 (m, 4 H) 7.55 - 7.59 (m, 1 H) 7.29 - 7.39 (m, 3 H) 7.19 - 7.24 (m, 1 H); MS (ESI) m/z 480 [M-I]".
  • 52
  • [ 98437-24-2 ]
  • [ 1154061-31-0 ]
  • [ 1154059-87-6 ]
YieldReaction ConditionsOperation in experiment
20% With potassium carbonate In tetrahydrofuran; water at 65℃; 103 4-Bromo-3-(hydroxymethyl)-N-(2-sulfamoylphenylsulfonyl)benzamide (0.1912 g, 0.43 mmol), benzofuran-2-ylboronic acid (0.0783 g, 0.48 mmol), potassium carbonate (0.2428 g, 1.76 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.0385 g, 0.05 mmol) in tetrahydrofuran (10 mL) and water (2 mL) was heated at 65° C. overnight. Water and ethyl acetate was added and the aqueous phase was acidified with hydrochloric acid (2 M). The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water, water/brine (1:1) and brine, dried over magnesium sulfate and the solvent was evaporated. Purification by preparative HPLC gave 0.042 g (20% yield) of the title compound.1H NMR (400 MHz, DMSO-d6) δ ppm 8.29-8.39 (m, 1H) 8.18 (s, 1H) 8.11-8.17 (m, 1H) 7.92-8.02 (m, 2H) 7.82-7.92 (m, 2H) 7.72 (s, 1H) 7.65 (s, 1H) 7.42 (d, 3H) 7.38 (s, 1H) 7.30 (s, 1H) 4.78 (s, 2H); MS (ESI) m/z 487.1 [M+H]+, 485.3 [M-H]-.
20% With potassium carbonate In tetrahydrofuran; water at 65℃; 103 4-Bromo-3-(hydroxymethyl)-N-(2-sulfamoylphenylsulfonyl)benzamide (0.1912 g, 0.43 mmol), benzofuran-2-ylboronic acid (0.0783 g, 0.48 mmol), potassium carbonate (0.2428 g, 1.76 mmol) and [l,r-bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.0385 g, 0.05 mmol) in tetrahydrofuran (10 mL) and water (2 mL) was heated at 65 0C overnight. Water and ethyl acetate was added and the aqueous phase was acidified with hydrochloric acid (2 M). The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water, water/brine (1:1) and brine, dried over magnesium sulfate and the solvent was evaporated. Purification by preparative HPLC gave 0.042 g (20% yield) of the title compound.1H NMR (400 MHz, DMSO-J6) δ ppm 8.29 - 8.39 (m, I H) 8.18 (s, I H) 8.11 - 8.17 (m, 1 H) 7.92 - 8.02 (m, 2 H) 7.82 - 7.92 (m, 2 H) 7.72 (s, 1 H) 7.65 (s, 1 H) 7.42 (d, 3 H) 7.38 (s, 1 H) 7.30 (s, 1 H) 4.78 (s, 2 H); MS (ESI) m/z 487.1 [M+H]+, 485.3 [M-H]".
  • 53
  • [ 98437-24-2 ]
  • [ 1154060-97-5 ]
  • [ 1154060-11-3 ]
YieldReaction ConditionsOperation in experiment
52% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.333333h; Microwave; 127 4-Bromo-3-isopropoxy-N-(2-sulfamoylphenylsulfonyl)benzamide (0.114 g, 0.24 mmol), benzofuran-2-ylboronic acid (0.077 g, 0.48 mmol) and 1,1'-bis(diphenylphosphino)ferrocene-palladium dichloride (0.020 g, 0.02 mmol) were dissolved in N,N-dimethylformamide under an atmosphere of argon followed by addition of aqueous sodium carbonate (0.358 mL, 0.72 mmol). The reaction mixture was heated in a microwave at 120° C. for 20 min under an atmosphere of argon and was then partitioned between water and ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2 M) and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by preparative HPLC gave 0.064 g (52% yield) of the title compound.1H NMR (500 MHz, DMSO-d6), δ ppm 8.35 (d, 1H) 8.15 (d, 1H), 8.01 (d, 1H), 7.88 (br. s., 2H), 7.69-7.78 (m, 2H), 7.62 (d, 1H), 7.53-7.60 (m, 2H), 7.46 (s, 2H), 7.31-7.40 (m, 1H) 7.23-7.31 (m, 1H), 4.91-5.03 (m, 1H), 1.46 (s, 3H), 1.45 (s, 3H); MS (ESI) m/z 513 [M-1]-.
52% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.333333h; Microwave irradiation; 127 4-bromo-3-isopropoxybenzoic acid (0.621 g, 2.40 mmol), N-(3-dimethylaminopropyl)-N'- ethylcarbodiimide hydrochloride (0.689 g, 3.60 mmol) and 4-dimethylaminopyridine (0.439 g, 3.60 mmol) were added to a solution of benzene- 1 ,2-disulfonamide (0.566 g, 2.40 mmol) in N,N-dimethylformamide (30 mL). The reaction mixture was stirred at room temperature over night and was then partitioned between water and ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2 M) and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using ethyl acetate as the eluent, gave 0.944 g (83% yield) of the title compound.1H NMR (500 MHz, CD3OD) δ ppm 8.39 (d, 1 H), 8.20 - 8.28 (m, 1 H), 7.73 - 7.79 (m, 2 H), 7.61 (s, 1 H), 7.56 (d, 1 H), 7.39 (dd, 1 H), 4.72 (dt, 1 H), 1.37 (s, 3 H), 1.35 (s, 3 H); MS (ESI) m/z Al 5, All [M-I]".
  • 54
  • [ 98437-24-2 ]
  • [ 1154061-06-9 ]
  • [ 1154060-29-3 ]
YieldReaction ConditionsOperation in experiment
68% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.333333h; Microwave; 145 4-bromo-3-(3-methoxy-3-methylbutoxy)-N-(2-sulfamoylphenylsulfonyl)benzamide (0.250 g, 0.47 mmol),benzofuran-2-ylboronic acid (0.151 g, 0.93 mmol) and 1,1'-bis(diphenylphosphino)ferrocene-palladium dichloride (0.038 g, 0.05 mmol) were dissolved in N,N-dimethylformamide (3 mL) under an atmosphere of argon. Aqueous sodium carbonate (0.700 mL, 1.40 mmol) was added, the reaction mixture was heated in a microwave at 120° C. for 20 min under an atmosphere of argon and was then partitioned between water and ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2 M) and extracted with ethyl acetate. The organic phase were dried over magnesium sulfate and the solvent was evaporated. Purification by preparative HPLC gave 0.181 g (68% yield) of the title compound.1H NMR (500 MHz, CD3OD) δ ppm 8.45-8.53 (m, 1H) 8.28 (dd, 1H) 8.09 (d, 1H) 7.80-7.91 (m, 2H) 7.71 (s, 1H) 7.64 (d, 1H) 7.58 (dd, 1H) 7.55 (s, 1H) 7.52 (d, 1H) 7.28-7.36 (m, 1H) 7.23 (t, 1H) 4.38 (t, 2H) 3.29 (s, 3H) 2.24 (t, 2H) 1.33 (s, 6H); MS (ESI) m/z571 [M-1]-.
68% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.333333h; Microwave irradition; 145 4-bromo-3 -(3 -methoxy-3 -methylbutoxy)-N-(2-sulfamoylphenylsulfonyl)benzamide (0.250 g, 0.47 mmol),benzofuran-2-ylboronic acid (0.151 g, 0.93 mmol) and 1,1'- bis(diphenylphosphino)ferrocene-palladium dichloride (0.038 g, 0.05 mmol) were dissolved in N,N-dimethylformamide (3 mL) under an atmosphere of argon. Aqueous sodium carbonate (0.700 mL, 1.40 mmol) was added, the reaction mixture was heated in a microwave at 120 0C for 20 min under an atmosphere of argon and was then partitioned between water and ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2 M) and extracted with ethyl acetate. The organic phase were dried over magnesium sulfate and the solvent was evaporated. Purification by preparative HPLC gave 0.181 g (68% yield) of the title compound.1H NMR (500 MHz, CD3OD) δ ppm 8.45 - 8.53 (m, 1 H) 8.28 (dd, 1 H) 8.09 (d, 1 H) 7.80 - 7.91 (m, 2 H) 7.71 (s, 1 H) 7.64 (d, 1 H) 7.58 (dd, 1 H) 7.55 (s, 1 H) 7.52 (d, 1 H) 7.28 - 7.36 (m, 1 H) 7.23 (t, 1 H) 4.38 (t, 2 H) 3.29 (s, 3 H) 2.24 (t, 2 H) 1.33 (s, 6 H); MS (ESI) m/z 571 [M-I]".
  • 55
  • [ 98437-24-2 ]
  • [ 1154061-09-2 ]
  • [ 1154060-31-7 ]
YieldReaction ConditionsOperation in experiment
24% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.5h; Microwave; 147 A mixture of 5,6-dichloro-N-(2-sulfamoylphenylsulfonyl)nicotinamide (164 mg, 0.40 mmol), 2-benzofuranboronic acid (84 mg, 0.52 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium dichloride (32.9 mg, 0.040 mmol), N,N-dimethylformamide (4 mL) and sodium carbonate (2 M, 0.60 mL, 1.20 mmol) under an atmosphere of argon was heated at 120° C. for 0.5 hour in a microwave. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by preparative HPLC gave 0.047 g (24% yield) of the title compound.1H NMR (DMSO-d6) δ ppm 8.96 (d, 1H) 8.37 (s, 1H) 8.26 (dd, 3.70 Hz, 1H) 8.05 (dd, 3.39 Hz, 1H) 7.88 (s, 1H) 7.73-7.80 (m, 3H) 7.66 (d, 1H) 7.37-7.50 (m, 3H) 7.26-7.31 (m, 1H); MS (ESI) m/z 490 [M-1]-.
24% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.5h; Microwave irradition; 147 A mixture of 5,6-dichloro-N-(2-sulfamoylphenylsulfonyl)nicotinamide (164 mg, 0.40 mmol), 2-benzofuranboronic acid (84 mg, 0.52 mmol), 1,1'- bis(diphenylphosphino)ferrocene-palladium dichloride (32.9 mg, 0.040 mmol), N,N- dimethylformamide (4 mL) and sodium carbonate (2 M, 0.60 mL, 1.20 mmol) under an atmosphere of argon was heated at 120 0C for 0.5 hour in a microwave. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by preparative HPLC gave 0.047 g (24% yield) of the title compound. 1H NMR (DMSO-J6) δ ppm 8.96 (d, 1 H) 8.37 (s, 1 H) 8.26 (dd, 3.70 Hz, 1 H) 8.05 (dd, 3.39 Hz, 1 H) 7.88 (s, 1 H) 7.73 - 7.80 (m, 3 H) 7.66 (d, 1 H) 7.37 - 7.50 (m, 3 H) 7.26 - 7.31 (m, 1 H); MS (ESI) m/z 490 [M-I]".
  • 56
  • [ 98437-24-2 ]
  • [ 1154061-22-9 ]
  • [ 1154061-21-8 ]
YieldReaction ConditionsOperation in experiment
25% With potassium carbonate In tetrahydrofuran; water at 150℃; for 0.25h; Microwave; 161.a 4-bromo-N-(4-((tert-butyldimethylsilyloxy)methyl)-2-(N-tert-butylsulfamoyl)phenylsulfonyl)benzamide (1.0 g, 1.61 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.130 g, 0.16 mmol), benzofuran-2-ylboronic acid (0.287 g, 1.78 mmol) and potassium carbonate (1.338 g, 9.68 mmol) were dissolved in tetrahydrofurane (14 mL) and water(1 mL). The reaction was irradiated for 15 min at 150° C. in a microwave, filtered through a plug of celite and concentrated in vacuo. Purification by column chromatography, using a gradient with increasing polarity (0 to 100% ethyl acetate in heptane) as the eluent, gave 0.266 g (25% yield) of the title compound.MS (ESI) m/z 655 [M-1]-
25% With potassium carbonate In tetrahydrofuran; water at 150℃; for 0.25h; Microwave irradiation; 161.a 4-bromo-N-(4-((tert-butyldimethylsilyloxy)methyl)-2-(N-tert- butylsulfamoyl)phenylsulfonyl)benzamide (1.0 g, 1.61 mmol), [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium (0.130 g, 0.16 mmol), benzofuran-2- ylboronic acid (0.287 g, 1.78 mmol) and potassium carbonate (1.338 g, 9.68 mmol) were dissolved in tetrahydrofurane (14 mL) and water(l mL). The reaction was irradiated for 15 min at 150 0C in a microwave, filtered through a plug of celite and concentrated in vacuo. Purification by column chromatography, using a gradient with increasing polarity (0 to 100 % ethyl acetate in heptane) as the eluent, gave 0.266 g (25% yield) of the title compound. MS (ESI) m/z 655 [M-I]"
  • 57
  • [ 98437-24-2 ]
  • [ 1161944-91-7 ]
  • (E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonic acid sodium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With water; sodium carbonate In N,N-dimethyl-formamide at 90℃; for 12h; 3.b 1-Bromo-4-[(E)-2-ethoxysulfonylethenyl]benzene (1.0 g, 3.4 mmol) and benzofuran-2-boronic acid (0.61 g, 3.7 mmol) were dissolved in DMF (20 mL). Sodium carbonate (2M, 10 mL) and tetrakis(triphenylphosphine) palladium(0) (200 mg, 0.17 mmol) were added and the resulting mixture was stirred under argon at 90° C. for 12 h. Water was added to the mixture and the resulting precipitate was collected, washed with water and dried to give the product as a sodium salt which was used in the next step without further purification (0.38 g, 35%).1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (d, 2H), 7.59-7.69 (m, 4H), 7.48 (s, 1H), 7.33 (td, 1H), 7.27 (td, 1H), 6.95 (s, 2H);ESMS: m/z [M-1]298.9.
  • 58
  • [ 98437-24-2 ]
  • [ 1161945-55-6 ]
  • [ 1161945-54-5 ]
YieldReaction ConditionsOperation in experiment
38% With caesium carbonate In 1,2-dimethoxyethane; water at 120℃; for 0.25h; Microwave irradiation; 204.b A mixture of (E)-N,N-diallyl-4-(2-(4-bromophenyl)vinylsulfonamido)pyridine-3-sulfonamide (0.47 g, 0.94 mmol), 2-benzofuranboronic acid (0.20 g, 1.23 mmol), (1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.039 g, 0.050 mmol), cesium carbonate (0.46 g, 1.41 mmol), 1,2-dimethoxyethane (9 mL) and water (1 mL) under an atmosphere of argon was heated at 120° C. for 15 min in a microwave. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (98:2) as the eluent, gave the title compound in 38% yield.1H NMR (DMSO-d6) δ ppm 13.03 (br s, 1H) 8.52 (d, 1H) 8.04 (dd, 1H) 7.96 (d, 2H) 7.83 (d, 2H) 7.67 (ddd, 2H) 7.57 (d, 1H) 7.43-7.51 (m, 2H) 7.25-7.41 (m, 3H) 5.60-5.73 (m, 2H) 5.00-5.15 (m, 4H) 3.87-3.96 (m, 4H); MS (ESI) m/z 534 [M-1]-
  • 59
  • [ 1104637-65-1 ]
  • [ 7732-18-5 ]
  • [ 98437-24-2 ]
YieldReaction ConditionsOperation in experiment
In not given hydrolysis of appropriate N-methyliminodiacetic acid boronate;
  • 60
  • [ 1104637-65-1 ]
  • [ 98437-24-2 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide In tetrahydrofuran; water at 23℃; for 0.333333h;
  • 61
  • [ 98437-24-2 ]
  • [ 4408-64-4 ]
  • [ 1104637-65-1 ]
YieldReaction ConditionsOperation in experiment
86% In dimethyl sulfoxide; toluene for 8h; Reflux;
86% In dimethyl sulfoxide; toluene for 8h; Inert atmosphere; Reflux; 1 To form protected organoboronic acid 2b, the general procedure was followed using benzofuran-2-boronic acid (5.247 g, 32.39 mmol, Sigma-Aldrich), N-methyl iminodiacetic acid (5.005 g, 34.02 mmol), toluene (135 mL) and DMSO (15 mL). The mixture was refluxed for 8 h. The product was eluted with Et2θ -> Et2θ:MeCN 2:1. The solid thus obtained was dissolved in a minimum of acetone, to which Et2θ was slowly added to promote crystallization. Filtration of the mixture afforded 2b as a colorless crystalline solid (7.61 g, 86%). TLC (EtOAc) Rf = 0.45, visualized by UV (254 nm) and KMnO4 stain. 1H-NMR (500 MHz, CD3CN) δ 7.63 (app dq, / = 7.5, 1.0 Hz, 1 H), 7.51 (app. dt, / = 8.5, 1.0 Hz, 1 H), 7.30 (m, 1 H), 7.22 (app tt, / = 7.5, 0.5 Hz, 1 H), 7.1 1 (s, 1 H), 4.14 (d, / = 17 Hz, 2H), 3.97 (d, / = 17 Hz, 2H), 2.69 (s, 3H). 13C-NMR (125 MHz, CD3CN) δ 169.2, 158.2, 129.1 , 125.7, 123.6, 122.4, 1 15.8, 1 12.2, 62.6, 48.1. 11 B-NMR (96 MHz, CD3CN) δ 9.5. HRMS (EI +) Calculated for C13H12BNOS (M) + : 273.0809, Found: 273.0810. IR (thin film, cm -1) 3008, 2956, 1765, 1560, 1448, 1335, 1282, 1249, 1 191 , 1 157, 1 138, 1052, 1005, 942, 853.
  • 62
  • [ 98437-24-2 ]
  • [ 18995-35-2 ]
  • [ 1158985-00-2 ]
  • 63
  • [ 98437-24-2 ]
  • [ 591-18-4 ]
  • 2-(3’-bromophenyl)benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium phosphate monohydrate; C41H64ClNPPd In tetrahydrofuran; water at 20℃; for 16h; Microwave irradiation; Inert atmosphere; General procedure: (method P2) To a dry microwave vial containing the aryl boronic acid and potassium triphosphate monohydrate (3.0 eq) under argon atmosphere, was added a solution of 2-bromo-allyl alcohol/bromide (1.0 eq) in THF. H20 was added and the mixture was degassed using nitrogen gas for 10 mins. The *Buchwald pre-catalyst (Gen I or Gen II) (2 mol%) was added and the mixture was further degassed for 5 mins before the sealed reaction mixture was heated at the optimized temperature (60 - 80 °C) for each compound for 16 h. When the reaction was completed, the solvents were removed in vacuo and the residue was partitioned between ethyl acetate and H20. The organic layer was washed twice with H20 and dried with MgS04. After filtration, the solvent was removed in vacuo to afford the crude product which was further purified by column chromatography. *Pd2(dba)3 (2mol%) and PPh3 (4 mol%) were used instead of the precatalyst when R group contains chlorine.
82% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;
81% With sodium carbonate In water; toluene for 10h; Inert atmosphere; Reflux; X-1.1-1 (1-1) Synthesis of 2-(3-bromophenyl)benzo[b]furan Under an argon atmosphere, 300 mL of toluene and 150 mL of a 2-M aqueous solution of sodium carbonate were added to 28.3 g (100 mmol) of 3-iodobromobenzene, 17.0 g (105 mmol) of benzofuran-2-boronic acid, and 2.31 g (2.00 mmol) of tetrakis(triphenylphosphine)paliadium(0), and the mixture was refluxed under heat for 10 hours. Immediatelyafter the completion of the reaction, the resultant was filtrated, and then the water layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography, whereby 22.1 g of the white crystal of 2- (3-bromophenyl)benzo [b] furan were obtained (81% yield).
  • 64
  • [ 98437-24-2 ]
  • [ 30289-28-2 ]
  • N-methoxy-N-methylbenzofuran-2-carboxamide [ No CAS ]
  • 65
  • [ 98437-24-2 ]
  • [ 696-62-8 ]
  • [ 19234-04-9 ]
YieldReaction ConditionsOperation in experiment
98% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 8h; Inert atmosphere;
98% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 8h; Inert atmosphere; 4.2.1. 2-Phenylbenzofuran (2a) General procedure: Following a modified procedure by Suzuki et al.,20 in a dry Schlenk benzofuran-2-boronic acid (200 mg, 1.23 mmol), iodobenzene (126 μL, 1.12 mmol), Pd(OAc)2 (24 mg, 0.11 mmol) and Na2CO3 (237 mg, 2.24 mmol) were placed under Argon, and acetone (6.6 mL) and water (7.7 mL) were added. The reaction mixture was stirred at room temperature until full consumption of the starting material was indicated by TLC (8 h). The reaction mixture was quenched with water and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtrated and concentrated to dryness in vacuo. The crude compound was purified by flash chromatography (silica, pentane/EtOAc 98:2) to afford 2-phenylbenzofuran (2a) as a white solid with 97% yield (211 mg, 1.08 mmol);
94% With palladium diacetate; potassium carbonate In methanol; polyethylene glycol 4000 at 50℃; for 1h; Inert atmosphere;
87% Stage #1: para-iodoanisole With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 20℃; for 0.333333h; Schlenk technique; Stage #2: benzofuran-2-boronic acid With sodium hydrogencarbonate In 1,4-dioxane for 2h; Reflux;
23% Stage #1: benzofuran-2-boronic acid; para-iodoanisole With potassium phosphate; nickel(II) nitrate hexahydrate; 1,1'-((1H-pyrrole-2,5-diyl)bis(methylene))bis(3-methyl-1H-imidazol-3-ium) diiodide In toluene at 20℃; for 0.0833333h; Sealed tube; Stage #2: In toluene at 160℃; for 4h; Sealed tube; 2. General procedure for the Suzuki-Miyaura cross-coupling reactions General procedure: Aryl iodide (1.0 mmol), arylboronic acid (2.0 mmol), Ni(NO3)26H2O (0.05 mmol), pre-ligand Pre-L1(0.05 mmol), base (3.0 mmol), and toluene (3 mL) were added to a glass tube, which was then sealed with aPTFE cap. After the reaction mixture was stirred vigorously at room temperature for 5 min, the sealed glasstube with the reaction mixture was placed in a Radleys Carousel 12 Plus Reaction Station, which waspreheated to the described temperature. After the reaction was stirred for the required time and then cooleddown to room temperature, water (10 mL) was added to the reaction mixture. The resulting mixture wasextracted with ethyl acetate (3 x 10 mL). The combined organic layers were dried over anhydrous Na2SO4,filtered and concentrated to dryness. The remaining residue was analyzed by GC (Table 1) or purified byflash chromatography on silica gel with ethyl acetate-hexanes (0-20% ethyl acetate in hexanes).
19% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 5h; Schlenk technique; Inert atmosphere;

  • 66
  • [ 98437-24-2 ]
  • [ 1243142-35-9 ]
  • [ 1243142-37-1 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; IX.3 Intermediate IX.2 (8.02 mmol), benzo(b)-flιran-2-boronic acid (12.03 mmol), tetrakis triphenylphosphine palladium (0.40 mmol), sodium carbonate (24.06 mmol) and H2O (0.8 ml) were mixed together in anhydrous DMF (8 ml) under nitrogen. After nitrogen purge the reaction mixture was stirred at 80 0C for 3 hours. EtOAC and water were added. Organics were separated, dried over sodium sulfate, concentrated in vacuo and purified by silica gel chromatography (DCM/MeOH) to give Intermediate IX.3 as a beige solid in 84 % yield, which was characterized by the following spectroscopic data: 1H NMR (CDCI3, 400 MHz) δ (ppm) 2.35 (s, 3H), 2.65 (s, 3H), 3.87 (d, J= 11.4 Hz, 3H), 6.02 (d, J= 6.20 Hz, IH), 6.40 (s, IH), 7.04-7.09 (m, 4H), 7.22 (t, J = 7.50 Hz, IH), 7.30 (t, J = 7.50, IH), 7.53 (d, J = 8.03 Hz, IH), 7.57-7.60 (m, 3H), 7.77 (dd, J = 7.80 Hz and J = 14.15 Hz, IH), 7.84 (d, J = 8.45 Hz, 2H), 31P NMR (CDCl3, 162 MHz) δ (ppm) 19.41 (s, IP); and MS (ESI, EI+) m/z = 474 (MH+).
  • 67
  • [ 98437-24-2 ]
  • [ 51554-93-9 ]
  • [ 1260184-88-0 ]
  • 68
  • [ 98437-24-2 ]
  • [ 126930-72-1 ]
  • [ 1260184-89-1 ]
  • 69
  • [ 98437-24-2 ]
  • [ 1255707-60-8 ]
  • [ 1255706-59-2 ]
YieldReaction ConditionsOperation in experiment
46% With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.333333h; Inert atmosphere; Microwave irradiation; 7 Example 7 4-(Benzofuran-2-yl)-3-(2,2-difluoroethoxy)-N-(2-sulfamoylphenylsulfonyl)benzamide2.0 M Aqueous sodium carbonate (0.625 rnL, 1.25 mmol) was added to a mixture of 4- bromo-3-(2,2-difluoroethoxy)-N-(2-sulfamoylphenylsulfonyl)benzamide (0.208 g, 0.42 mmol), benzofuran-2-ylboronic acid (0.135 g, 0.83 mmol), 1,1'- bis(diphenylphosphino)ferrocene-palladium dichloride (0.034 g, 0.04 mmol) in N5N- dimethylformamide (3 mL) under an atmosphere of argon. The reaction mixture was heated in a microwave at 120 0C for 20 min under an atmosphere of argon. The reaction mixture was partitioned between water and ethyl acetate. The aqueous phase was acidified with 2.0 M aqueous hydrochloric acid and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by preparative HPLC gave 0.104 g (46% yield) of the title compound. 1H NMR (500 MHz, DMSO-J6) δ ppm 8.37 (d, 1 H), 8.16 (d, 1 H), 8.06 (d, 1 H), 7.85 - 7.95 (m, 2 H), 7.77 (s, 1 H), 7.67 - 7.75 (m, 2 H), 7.65 (d, 1 H), 7.52 (s, 1 H), 7.45 (s, 2 H), 7.35 - 7.41 (m, 1 H), 7.29 (t, 1 H), 6.53 - 6.81 (m, 1 H), 4.63 (td, 2 H); MS (ESI) m/z 535 [M-I]".
  • 70
  • [ 98437-24-2 ]
  • [ 1255707-85-7 ]
  • [ 1255707-84-6 ]
YieldReaction ConditionsOperation in experiment
46% With sodium hydrogencarbonate In 1,2-dimethoxyethane; ethanol; water at 100℃; Sealed tube; 75.a; 76.a a) 4-Methoxy-benzene-l,2-disulfonic acid l-(4-benzofuran-2-yl-benzoylamide)2-tert-butylamideTo a degassed solution of 4-methoxy-benzene-l,2-disulfonic acid l-(4-bromo- benzoylamide) 2-tert-butylamide (0.80 g, 1.58 mmol) in dimethoxyethane (32 mL) was added a solution of benzo[b]furan-2-boronic acid (0.36 g, 2.22 mmol) in a mixture of dimethoxyethane (7.2 mL) and ethanol (2.4 mL) followed by sodium bicarbonate (2 M aqueous, 4.8 mL, 9.50 mmol) and [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium (dichloromethane complex) (0.13 g, 0.16 mmol). The reaction mixture was degassed for 15 minutes and heated in a sealed tube at 100 0C overnight. The reaction mixture was cooled to room temperature, filtered through a pad of Celite and concentrated under reduced pressure. Purification by column chromatography, using a gradient of 30-70% ethyl acetate in hexane as the eluent, gave 397 mg (46% yield) of the title compound. 1H NMR (400 MHz, DMSO-J6) δ ppm 8.26 (d, 1 H) 7.99 (s, 4 H) 7.54 - 7.71 (m, 4 H) 7.32 - 7.40 (m, 2 H) 7.24 - 7.31 (m, 1 H) 7.16 (br. s., 1 H) 3.90 (s, 3 H) 1.11 - 1.19 (m, 9 H); MS (ESI) m/z 541 [M-I]".
  • 71
  • [ 98437-24-2 ]
  • [ 128455-62-9 ]
  • [ 1251914-07-4 ]
YieldReaction ConditionsOperation in experiment
98% With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In tetrahydrofuran; water at 40℃; for 2h; Inert atmosphere;
  • 72
  • [ 98437-24-2 ]
  • [ 13223-25-1 ]
  • [ 1251914-08-5 ]
YieldReaction ConditionsOperation in experiment
97% With (eta3-indenyl)Pd(XPhos)(OTf); potassium carbonate; In tetrahydrofuran; methanol; at 40℃; for 1h;Glovebox; Sealed tube; Cooling with ethanol-dry ice; In a dinitrogen filled glove box, <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (175 1iL, 1.0 mmol), benzofuran-2-boronic acid (243 mg, 1.5 mmol), K2C03 (276 mg, 2.0 mmol) and (3 indenyl)Pd(XPhos)(OTf) (8.4 mg, 0.01 mmol) were added to a 4 dram vial equipped with a magnetic stir bar. Methanol (4 mL) and THF (2 mL) were added to the vial, which was then sealed and stirred outside of the glove box at 40C for one hour. At this point, the vial wasopened to air and diethyl ether (10 mL) and H20 (10 mL) were added to the reaction mixture. The aqueous phase was extracted with diethyl ether (3 x 10 mL). The combined organic phases were dried over MgSO4 and filtered. The supernatant was then passed through a pad of silica gel, followed by removal of the solvent under reduced pressure to give the organic product. Yield: 249 mg, 97%.
  • 73
  • [ 98437-24-2 ]
  • [ 36282-26-5 ]
  • [ 1268822-57-6 ]
YieldReaction ConditionsOperation in experiment
59% With sodium carbonate In 1,2-dimethoxyethane; water for 5h; Heating; Reflux; 2-(Benzofuran~2-yl)~4-fluorobenzonitriIe (AUPOl 158-1)A mixture of 2-bromo-4-fluorobenzonitrile (5,15 g, 25.65 mmol), benzofuran-2- ylboronic acid (5.0 g, 30,8 mmol), 1 ,2-dimethoxyethane (25 mL) and 2M Na2CO3 (40 niL) was heated to reflux before Pd2(dba)3 (100 mg) was added and heating was continued for 5 h. After cooling to r.t, EtOAc (20 mL) was added to dissolve the product. The mixture was filtered through celite, the organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure, The residue was dissolved in minimum amount of CHCl3 and passed through Silica. Solvent was evaporated and the residue was first purified by crystallisation from a mixture CHCI3/PE (98/2). The filtrate was purified by Combiflash chromatography (40 g column, 13 g Silica, gradient of eluent from PE to PE/EtOac 9/1) to give the title compound as light yellow solid purified by rinsing with PE to give at the end a white solid (5.15 g), This solid had to be purified an ultimate time by drying under vacuum at 80 0C for O/N. Finally, pure expected compound was obtained as a off-white solid in 59% yield (3.6 g); mp 123-124 0C; 1H NMR (270 MHz, CDCl3) .57.13 (IH, td, J = 2.5 and 7.3 Hz, ArH), 730 (IH, X, J = 1.1 Hz5 ArH), 7,40 (IH, X, J = 1.1 Hz, ArH), 7.56 (IH5 d, J = 7.7 Hz, ArH), 7,69 (IH, d, J = 7.7 Hz, ArH), 7.76-7.86 (3H, m, ArH); Anal. Calcd. for Ci5H8FNO: C 75,94, H 3.40, N 5.90. Found: C 75,70, H 3.37, N 5.97 %.
  • 74
  • [ 98437-24-2 ]
  • [ 1268867-67-9 ]
  • [ 1268867-30-6 ]
YieldReaction ConditionsOperation in experiment
63% With potassium phosphate In 1,4-dioxane at 100℃; Sealed tube; 89.1 Into a 10-mL sealed tube, was placed methyl 2-chloro-3- (isopropyl(methyl)amino)quinoxaline-6-carboxylate (200 mg, 0.68 mmol, 1.00 equiv), benzofuran-2-ylboronic acid (220 mg, 1.36 mmol, 1.99 equiv), Pd(PPh3)4 (157 mg, 0.14 mmol, 0.20 equiv), K3P04 (577 mg, 2.73 mmol, 4.01 equiv), 1,4- dioxane (4 mL). The resulting solution was stirred for overnight at 100°C in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:40). This resulted in 160 mg (63%) of methyl 2-(benzofuran-2-yl)-3- (isopropyl(methyl)amino)quinoxaline-6-carboxylate as a yellow solid.LC-MS: (ES, m/z): 376 [M+H] +
63% With potassium phosphate In 1,4-dioxane at 100℃; Sealed vessel; 7 EXAMPLE 7 Methyl 2-(benzofuran-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate Into a 10-mL sealed tube, was placed methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (200 mg, 0.68 mmol, 1.00 equiv), benzofuran-2-ylboronic acid (220 mg, 1.36 mmol, 1.99 equiv), Pd(PPh3)4 (157 mg, 0.14 mmol, 0.20 equiv), K3PO4 (577 mg, 2.73 mmol, 4.01 equiv), and 1,4-dioxane (4 mL). The resulting solution was stirred for overnight at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:40). This resulted in 160 mg (63%) of methyl 2-(benzofuran-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a yellow solid.LC-MS: (ES, m/z): 376 [M+H]+
  • 75
  • [ 98437-24-2 ]
  • [ 1296269-71-0 ]
  • [ 1296269-89-0 ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 90 - 120℃; regioselective reaction; 4.4. General procedure for Suzuki cross-coupling of aryl/heteroaryl boronic acids with 1,3-(or 1,5)-diphenyl-4-halo-5-(or 3-)(methylthio)pyrazoles 5a,b and 6a,b: synthesis of 1,3-(or 1,5-)diphenyl-4-aryl/heteroaryl-5-(or 3-)(methylthio)pyrazoles 7a-j and 8a-j General procedure: In a typical experiment, a mixture of 4-halopyrazole 5a,b or 6a,b (1.27 mmol), aryl/heteroaryl boronic acids 11a-j (1.90 mmol), Pd(PPh3)4 (146 mg, 0.127 mmol), EtOH (3.0 mL), and 2 M solution of aq Na2CO3 (3.0 mL) in toluene (8.0 mL) was heated at 90-120 °C for 10-12 h (monitored by TLC). The reaction mixture was then poured into 30 mL of cold water and extracted with CHCl3 (3×30 mL). The combined organic extracts were washed with water (2×50 mL), brine (1×30 mL), and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give products, which were purified by column chromatography over silica gel using hexane/EtOAc as eluent (7.5:2.5).
  • 76
  • [ 98437-24-2 ]
  • [ 1296269-70-9 ]
  • [ 1296269-79-8 ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 90 - 120℃; regioselective reaction; 4.4. General procedure for Suzuki cross-coupling of aryl/heteroaryl boronic acids with 1,3-(or 1,5)-diphenyl-4-halo-5-(or 3-)(methylthio)pyrazoles 5a,b and 6a,b: synthesis of 1,3-(or 1,5-)diphenyl-4-aryl/heteroaryl-5-(or 3-)(methylthio)pyrazoles 7a-j and 8a-j General procedure: In a typical experiment, a mixture of 4-halopyrazole 5a,b or 6a,b (1.27 mmol), aryl/heteroaryl boronic acids 11a-j (1.90 mmol), Pd(PPh3)4 (146 mg, 0.127 mmol), EtOH (3.0 mL), and 2 M solution of aq Na2CO3 (3.0 mL) in toluene (8.0 mL) was heated at 90-120 °C for 10-12 h (monitored by TLC). The reaction mixture was then poured into 30 mL of cold water and extracted with CHCl3 (3×30 mL). The combined organic extracts were washed with water (2×50 mL), brine (1×30 mL), and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give products, which were purified by column chromatography over silica gel using hexane/EtOAc as eluent (7.5:2.5).
  • 77
  • [ 98437-24-2 ]
  • cis-2-bromovinylboronic acid MIDA ester [ No CAS ]
  • C15H14BNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine; silver(l) oxide In tetrahydrofuran at 23℃; for 24h; Inert atmosphere; stereospecific reaction; 4.15. MIDA boronate 15e 4.15.1. Preparation of catalyst solutionIn a glovebox, to a 7 mL vial equipped with a stir bar and charged with P(o-tolyl)3 (11.7 mg, 0.04 mmol) and Pd2(dba)3 (9.3 mg, 0.01 mmol) was added THF (2 mL). The solution was stirred at 23 °C for 10 min.4.15.2. The freshly prepared catalyst solution was used in the following reactionIn a glovebox, to a 7 mL vial equipped with a stir bar and charged with MIDA boronate (Z)-Br-1(46.6 mg, 0.18 mmol), boronic acid 14e (66.1 mg, 0.41 mmol), and Ag2O (143.5 mg, 0.62 mmol) was added the prepared catalyst solution in one portion. The vial was sealed with a cap and removed from the glovebox. The solution was stirred in a subdued light environment at 23 °C for 24 h. The reaction mixture was filtered through a pad of Celite, concentrated in vacuo, dry loaded onto Celite from an acetone solution, and purified via flash chromatography on silica gel (Et2O/acetone 100:0→3:1) to afford MIDA boronate 15e as a pale yellow solid (49.1 mg, 92%).1H NMR (500 MHz, acetone-d6) δ 7.58 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.5 Hz, 1H), 7.29 (t, J=7.5 Hz, 1H), 7.21 (t, J=7.5 Hz, 1H), 7.04 (br d, J=15.5 Hz, 1H), 6.88 (s, 1H), 5.75 (d, J=15.5 Hz, 1H), 4.38 (d, J=17.0 Hz, 2H), 4.24 (d, J=17.0 Hz, 2H), 3.11 (s, 3H). 13C NMR (125 MHz, acetone-d6) δ 169.5, 156.1, 155.7, 131.2, 129.4, 125.6, 123.9, 122.0, 112.0, 108.6, 64.4, 48.9. HRMS (ESI+) calculated for C15H15BNO5 (M+H)+: 300.1043. Found: 300.1045.
  • 78
  • [ 98437-24-2 ]
  • [ 1312814-91-7 ]
  • [ 1312814-92-8 ]
YieldReaction ConditionsOperation in experiment
70% With tripotassium phosphate hexahydrate In 1,4-dioxane at 140℃; for 0.75h; Inert atmosphere; Irradiation with microwave; 1_1.6 A mixture of tert-butyl 2'-(2-chloropyrimidin-4-yl)-5'-(4-methoxybenzyl)-4'-oxo- 1^4',5',6'-tetrahydrospiro[piperidine-4,7'-pyrrolo[3,2-c]pyridine]-l-carboxylate (A5) (4.5 g, 8.36 mmol), 2-benzofuranboronic acid (4.06 g, 25.09 mmol) and potassium phosphate tribasic heptahydrate (8.49 g, 25.09 mmol) was dissolved in anhydrous dioxane (105 mL). The resulting solution was purged with nitrogen, followed by addition of l,l'-bis(diphenylphosphino)ferrocene palladium(II)chloride (676 mg, 0.836 mmol). The resulting mixture was again purged with nitrogen and stirred at 140 °C for 45 min in the microwave. After cooling to room temperature, the reaction mixture was diluted with EtOAc, washed three times with aqueous NaHC03, once with brine, dried over Na2S04, filtered and concentrated under vacuum. The crude product was triturated with toluene which gave tert-butyl 2'-(2-(benzofuran-2-yl)pyrimidin-4-yl)-5'- (4-methoxybenzyl)-4'-oxo- ,4',5',6'-tetrahydrospiro[piperidine-4,7'-pyrrolo[3,2- c]pyridine]-l-carboxylate (A6) as a white solid (3.60 g, 70 %). 1H NMR (400 MHz, DMSO-D6, 300K): δ = 1.42 (9H, s), 1.55 (2H, br d, J = 13.0 Hz), 2.08 (2H, br dt, J = 13.4 Hz), 2.65 (2H, br s), 3.56 (2H, br s), 3.74 (3H, s), 3.80 (2H, br s), 4.57 (2H, br s), 6.92 (2H, d, J = 8.6 Hz), 7.31 (2H, d, J= 8.6 Hz), 7.35 (1H, t, J = 7.6 Hz), 7.43 (1H, s), 7.46 (1H, t, J = 7.8 Hz), 7.75 (1H, d, J = 8.2 Hz), 7.80 (1H, d, J = 5.5 Hz), 7.82 (1H, d, J = 7.7 Hz), 8.03 (1H, s), 8.77 (1H, d, J = 5.4 Hz), 11.75 (1H, s). MS (ES) C36H37N505 requires: 619, found: 620.2 [M+H]+.
  • 79
  • [ 98437-24-2 ]
  • [ 1312478-54-8 ]
  • [ 1312479-09-6 ]
YieldReaction ConditionsOperation in experiment
42.8% With potassium carbonate In 1,4-dioxane; water at 90℃; Microwave irradiation; 33.A Pd EnCat (130 mg, 0.051 mmol) was added to a mixture of potassium carbonate (221 mg, 1.60 mmol), 1-benzofuran-2-ylboronic acid (271 mg, 0.954 mmol), and 4-(4-iodo-2- oxopyridin-1 (2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2- yloxy)butanamide, which may be produced as in Preparation 2A (240 mg, 0.63 mmol) in dioxane:water (5 mL, 4:1 ) in a 2-5 mL microwave vial and the reaction was heated at 90°C overnight. The reaction was filtered and the resin was washed with ethyl acetate (50 mL) and water (50 mL). The filtrate was concentrated to dryness and the crude was purified via flash chromatography on an Analogix SF15-12g column and eluted with ethyl acetate in heptane (0-80%) to afford the title compound as a white solid (105 mg, 42.8%). LC-MS m/z 487.7 (M-1 ).
  • 80
  • [ 98437-24-2 ]
  • [ 24386-93-4 ]
  • [ 1252858-13-1 ]
  • 81
  • [ 17530-69-7 ]
  • [ 98437-24-2 ]
  • [ 1352124-37-8 ]
YieldReaction ConditionsOperation in experiment
87% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; cesium fluoride In isopropyl alcohol at 85℃; for 10h; Inert atmosphere;
  • 82
  • [ 98437-24-2 ]
  • [ 1354742-59-8 ]
  • [ 1354742-91-8 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water at 150℃; for 0.5h; Inert atmosphere; Microwave irradiation; 4.1.1.16. 4-(Benzofuran-2-yl)-2-(carboxymethyl)benzoic acid (25e) General procedure for Suzuki coupling: 450 mg (1.47 mmol) of iodo derivative 16 or 24, boronic acid (2.4 mmol, 1.6 equiv), 40 mg (0.035 mmol) of Pd(PPh3)4 and 750 mg (5.4 mmol) of K2CO3 were mixed with 3 mL of aq EtOH (v/v = 1:1) and subjected to microwave reactor at 150 °C for 30 min. The resulting mixture was then evaporated to remove EtOH. The residue as an aqueous solution was filtered through glass wool while hot. The glass wool was washed several times with boiling aq K2CO3 (10% w/v). Combined filtrates were acidified (to pH 1) with 2 N aq HCl to give precipitate, which was collected by filtration, washed with water and dried overnight at rt.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water at 150℃; for 0.5h; Microwave irradiation;
  • 83
  • [ 98437-24-2 ]
  • 2-(carboxymethyl)-5-iodobenzoic acid [ No CAS ]
  • [ 1354742-86-1 ]
YieldReaction ConditionsOperation in experiment
87% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water at 150℃; for 0.5h; Inert atmosphere; Microwave irradiation; 4.1.1.11. 5-(Benzofuran-2-yl)-2-(carboxymethyl)benzoic acid (17f) General procedure for Suzuki coupling: 450 mg (1.47 mmol) of iodo derivative 16 or 24, boronic acid (2.4 mmol, 1.6 equiv), 40 mg (0.035 mmol) of Pd(PPh3)4 and 750 mg (5.4 mmol) of K2CO3 were mixed with 3 mL of aq EtOH (v/v = 1:1) and subjected to microwave reactor at 150 °C for 30 min. The resulting mixture was then evaporated to remove EtOH. The residue as an aqueous solution was filtered through glass wool while hot. The glass wool was washed several times with boiling aq K2CO3 (10% w/v). Combined filtrates were acidified (to pH 1) with 2 N aq HCl to give precipitate, which was collected by filtration, washed with water and dried overnight at rt.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water at 150℃; for 0.5h; Microwave irradiation;
  • 84
  • [ 98437-24-2 ]
  • [ 352-34-1 ]
  • [ 69976-38-1 ]
YieldReaction ConditionsOperation in experiment
93% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 8h; Inert atmosphere;
93% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 8h; Inert atmosphere; 4.2.1. 2-Phenylbenzofuran (2a) General procedure: Following a modified procedure by Suzuki et al.,20 in a dry Schlenk benzofuran-2-boronic acid (200 mg, 1.23 mmol), iodobenzene (126 μL, 1.12 mmol), Pd(OAc)2 (24 mg, 0.11 mmol) and Na2CO3 (237 mg, 2.24 mmol) were placed under Argon, and acetone (6.6 mL) and water (7.7 mL) were added. The reaction mixture was stirred at room temperature until full consumption of the starting material was indicated by TLC (8 h). The reaction mixture was quenched with water and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtrated and concentrated to dryness in vacuo. The crude compound was purified by flash chromatography (silica, pentane/EtOAc 98:2) to afford 2-phenylbenzofuran (2a) as a white solid with 97% yield (211 mg, 1.08 mmol);
  • 85
  • [ 98437-24-2 ]
  • [ 455-13-0 ]
  • 2-(4’-trifluoromethylphenyl)benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 5h; Schlenk technique; Inert atmosphere;
82% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 8h; Inert atmosphere;
82% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 8h; Inert atmosphere; 4.2.1. 2-Phenylbenzofuran (2a) General procedure: Following a modified procedure by Suzuki et al.,20 in a dry Schlenk benzofuran-2-boronic acid (200 mg, 1.23 mmol), iodobenzene (126 μL, 1.12 mmol), Pd(OAc)2 (24 mg, 0.11 mmol) and Na2CO3 (237 mg, 2.24 mmol) were placed under Argon, and acetone (6.6 mL) and water (7.7 mL) were added. The reaction mixture was stirred at room temperature until full consumption of the starting material was indicated by TLC (8 h). The reaction mixture was quenched with water and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtrated and concentrated to dryness in vacuo. The crude compound was purified by flash chromatography (silica, pentane/EtOAc 98:2) to afford 2-phenylbenzofuran (2a) as a white solid with 97% yield (211 mg, 1.08 mmol);
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