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[ CAS No. 106-37-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 106-37-6
Chemical Structure| 106-37-6
Chemical Structure| 106-37-6
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Quality Control of [ 106-37-6 ]

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Product Details of [ 106-37-6 ]

CAS No. :106-37-6 MDL No. :MFCD00000089
Formula : C6H4Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :SWJPEBQEEAHIGZ-UHFFFAOYSA-N
M.W : 235.90 Pubchem ID :7804
Synonyms :

Calculated chemistry of [ 106-37-6 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.84
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 3.79
Log Po/w (WLOGP) : 3.21
Log Po/w (MLOGP) : 3.79
Log Po/w (SILICOS-IT) : 3.25
Consensus Log Po/w : 3.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.25
Solubility : 0.0134 mg/ml ; 0.0000568 mol/l
Class : Moderately soluble
Log S (Ali) : -3.48
Solubility : 0.0774 mg/ml ; 0.000328 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.11
Solubility : 0.0184 mg/ml ; 0.000078 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.45

Safety of [ 106-37-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P273-P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362 UN#:N/A
Hazard Statements:H315-H319-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 106-37-6 ]

* 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 [ 106-37-6 ]

[ 106-37-6 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 106-37-6 ]
  • [ 106-94-5 ]
  • [ 4815-57-0 ]
  • 2
  • [ 106-37-6 ]
  • [ 108-95-2 ]
  • [ 101-55-3 ]
YieldReaction ConditionsOperation in experiment
To 200 ml toluene, 94g phenol and 80 g 50% caustic soda lye are added and water is azeotropically distilled out. 50 ml DMF and 475 g paradibromo benzene (PDBB) and 5 g cuprous bromide are added to it. The mass is maintained at 160-165C for 5 hours by distilling toluene. The mass is filtered at 80C, washed with toluene and the filtrate fractionally distilled under vacuum to give 229 g 4-bromodiphenyl ether, 99% purity, b.p. - 125C/2 mm
  • 3
  • [ 630-18-2 ]
  • [ 106-37-6 ]
  • [ 30314-45-5 ]
  • 4
  • [ 106-37-6 ]
  • [ 54458-61-6 ]
  • C24H34O2 [ No CAS ]
  • 5
  • [ 106-37-6 ]
  • [ 19524-06-2 ]
  • [ 39795-60-3 ]
  • 6
  • [ 106-37-6 ]
  • [ 118062-05-8 ]
  • [ 146655-85-8 ]
  • 1,4-bis(2',3',4'-trimethoxyphenyl)benzene [ No CAS ]
  • 8
  • [ 106-37-6 ]
  • [ 100-52-7 ]
  • [ 29334-16-5 ]
  • 10
  • [ 19230-28-5 ]
  • [ 124-38-9 ]
  • [ 106-37-6 ]
  • 4,4''-Dibromo-[1,1';3',1'']terphenyl-2'-carboxylic acid [ No CAS ]
  • 11
  • [ 106-37-6 ]
  • [ 20607-43-6 ]
  • [ 70398-89-9 ]
  • 12
  • [ 106-37-6 ]
  • [ 2716-23-6 ]
  • 2-p-Bromphenyl-2-bicyclo<2.2.2>octanol [ No CAS ]
  • 13
  • [ 106-37-6 ]
  • [ 28165-52-8 ]
  • 16
  • [ 110-91-8 ]
  • [ 106-37-6 ]
  • [ 92-53-5 ]
  • [ 30483-75-1 ]
  • 17
  • [ 106-37-6 ]
  • [ 100-67-4 ]
  • copper bronze [ No CAS ]
  • [ 101-55-3 ]
  • 18
  • [ 106-37-6 ]
  • [ 17049-50-2 ]
  • [ 106418-67-1 ]
  • 19
  • [ 106-37-6 ]
  • [ 40972-86-9 ]
  • 2,2'',3,3''-Tetramethoxy-1,1:4',1''-terphenyl [ No CAS ]
  • 20
  • [ 69814-56-8 ]
  • [ 106-37-6 ]
  • 4-bromo-bicyclo[4.2.0]octa-1,3,5-trien-7-one [ No CAS ]
  • 3-bromobicyclo[4.2.0]octa-1,3,5-trien-7-one [ No CAS ]
  • 21
  • [ 69814-56-8 ]
  • [ 106-37-6 ]
  • C12H13BrO2 [ No CAS ]
  • C12H13BrO2 [ No CAS ]
  • 22
  • [ 69814-56-8 ]
  • [ 106-37-6 ]
  • C18H22O4 [ No CAS ]
  • 24
  • [ 123-75-1 ]
  • [ 106-37-6 ]
  • [ 22090-26-2 ]
  • 25
  • [ 106-37-6 ]
  • [ 321724-19-0 ]
  • [ 174303-53-8 ]
  • 26
  • [ 106-37-6 ]
  • [ 189628-37-3 ]
  • [ 784144-30-5 ]
  • 27
  • [ 31608-22-7 ]
  • [ 106-37-6 ]
  • [ 212961-44-9 ]
  • 28
  • [ 106-37-6 ]
  • [ 89787-12-2 ]
  • 1,4-bis(2-isopropylphenyl)benzene [ No CAS ]
  • 29
  • [ 110-91-8 ]
  • [ 106-37-6 ]
  • [ 30483-75-1 ]
  • [ 4096-22-4 ]
  • 30
  • [ 106-37-6 ]
  • [ 40430-66-8 ]
  • 1,4-bis[2-(1-adamantyl)ethynyl]benzene [ No CAS ]
  • 31
  • [ 288-32-4 ]
  • [ 106-37-6 ]
  • [ 10040-96-7 ]
YieldReaction ConditionsOperation in experiment
90% With copper(l) iodide; caesium carbonate; dimethylbiguanide; In N,N-dimethyl-formamide; at 20 - 110℃; for 15.1667h; General procedure: A 25 mL flask with a magnetic stirring bar was charged with CuI(9.6 mg, 0.05 mmol), metformin (0.1 mmol), Cs2CO3 (652 mg,2.0 mmol), imidazole (1.0 mmol), an aryl halide (1.1 mmol), andDMF (5 mL). The mixture was stirred for 10 min at room temperature,and then heated to 110?C for the appropriate amount of time(see Table 2). The progress of the reaction was monitored by TLC.After completion of the reaction, the mixture was extracted with EtOAc (5 1 mL) and the organic phase separated and evaporated. Further purification by column chromatography gave the desired coupled product.
85% With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Catalytic behavior; General procedure: A mixture of aryl halide (2.4 mmol) and Cs2CO3(4.0 mmol,0.650 g), nitrogen-containing heterocycle (2.0 mmol), dry DMF(3 mL) solvent and catalyst was stirred at 100C in an oil bath under air. After cooling to room temperature, catalyst was first separated out by centrifugation and the liquid part was extracted with water and diethylether (2 × 15 mL). The organic layers thus collected were combined and washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified bycolumn chromatography on silica gel (mesh 60-120) using an n-hexane/ethylacetate mixture as the eluent to collect the desiredproduct. The product was analyzed by 1H and13C NMR and mass spectroscopy.
81% With C40H34CuIN6O6; sodium hydroxide; In dimethyl sulfoxide; at 100℃; for 4h;Sealed tube; General procedure: For the catalysis reaction, the catalyst C1 (12 mg,0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.
  • 32
  • [ 106-37-6 ]
  • [ 101-55-3 ]
  • 33
  • [ 106-37-6 ]
  • [ 10040-96-7 ]
  • 37
  • [ 110-91-8 ]
  • [ 106-37-6 ]
  • [ 30483-75-1 ]
YieldReaction ConditionsOperation in experiment
92% With potassium hydroxide; at 60℃; for 0.5h;Green chemistry;Catalytic behavior; General procedure: In a round-bottomed flask equipped with mechanical stirrer,aryl halide (1 mmol), amine (1.2 mmol), catalyst (5 mg) and KOH(2 mmol) were stirred in ethanol (5 ml) under air atmosphere at 60C for 0.5 h. The progress of the reaction was monitored by TLC and GC. After completion of the reaction, CH2Cl2 (15 ml) was added and the catalyst was separated using an external magnet. The organic layer was washed with water (3 x 10 ml) and dried over anhydrous MgSO4. The product was isolated by column chromatography (nhexaneeethylacetate, 5:1) to afford the corresponding products.The products were characterized by their physical properties,melting points, and FT-IR, 1H NMR and 13C NMR [69-71].
56% With tris-(dibenzylideneacetone)dipalladium(0); (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 80℃; for 16h;Sealed tube; Inert atmosphere; To a 50 mL sealed tube were added R-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.20 g, 0.31 mmol), tris(dibenzylideneacetone)dipalladium (0.095 g, 0.10 mmol), sodium tert-butoxide (0.49 g, 5.0 mmol), p-dibromobenzene (1.00 g, 4.15 mmol) and morpholine (0.37 mL, 4.2 mmol), then anhydrous toluene (8 mL) was added under nitrogen protection. The resulting mixture was stirred for 16 h at an oil bath temperature of 80C. The reaction mixture was cooled to rt and to the mixture was added EtOAc (20 mL). The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (PE:EtOAc=15:1, V/V)to give a white solid (0.56 g, 56%). MS(ESI, pos.ion)m/z:242.00(M+1)
47% With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 16h;Inert atmosphere; Reflux; A solution of tris(dibenzylideneacetone)dipalladium(0) (0.093 g, 0.1 mmol) and (±)-BINAP (0.13 g, 0.21 mmol) in toluene (7 mL) was degassed with argon for 10 min and then heated at 110 C for 15 min. The reaction mixture was allowed to cool to room temperature before potassiumtert-butoxide (0.53 g, 4.73 mmol), 1,4-dibromobenzene (80) (0.6 g, 2.54 mmol) and morpholine (332 muL, 3.82 mmol) were added. The resulting mixture was heated at reflux for 16 h, cooled to room temperature and filtered through a pad of Celite, the pad was further washed with toluene (30 mL) and the combined filtrates evaporated under reduced pressure to give the crude product. Purification by flash chromatography on silica eluting with hexane-ethyl acetate (6:1) gave the desired amine81(0.19 g, 47%) as a colourless solid; mp 110-111 C;numax/cm-12965, 2857, 2831, 1589, 1495, 1259, 1236, 1120, 923, 818; deltaH(300 MHz, CDCl3) 7.35 (2 H, d,J9.0 Hz), 6.78 (2 H, d,J9.0 Hz), 3.84 (4 H, t,J6.0 Hz), 3.11 (4 H, t,J6.0 Hz);deltaC(75 MHz, CDCl3) 150.3, 132.0, 117.4, 112.3, 66.8, 49.3;m/z(APCI) 242/244 ([M + H]+, 68/100).
26.96% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; johnphos; In 1,4-dioxane; at 100℃; for 12h;Sealed tube; Inert atmosphere; To a stirred solution of morpholine (2.0 g, 23.0 mmol), 1, 4-dibromo benzene (19.4 g,82.2 mmol) and 1,4-dioxane (10.0 mL) in sealed tube, 0s2003 (22.4 g, 68.7 mmol)was added and degasified with argon. To the above solution Pd2(dba)3 (0.2 g, 0.22mmol) and 2-(di-tert-butylphosphino)biphenyl (0.6 g, 2.0 mmol) was added andheated at 100 00 for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate, the organic layer was washed with water, brine solution and dried. Finally, concentrated under vacuo and purified by the column chromatography to yield the desired product (1 .5 g, 26.96%) as a yellow solid. LCMS: (M+2) =244.0; 1HNMR: (ODd3, 300MHz) 6 7.34-7.37 (d, 2H), 6.76-6.79 (d, 2H), 3.84-3.87 (t, 4H),3.10-3.13 (t, 4H).
With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); johnphos; In 1,4-dioxane; for 20h;Heating / reflux; EXAMPLE 35; Synthesis of (2S)-N-(Cyanomethyl)-4-methyl-2-[(R)-(4'-morpholin-4-yl-1,1 '-biphenyl-4-yl)(phenyl)methyl]oxy}pentanamide; Step 1; 4-(4-Bromophenyl)morpholine;To a solution of of morpholine (0.85 mmol, 739 mg) in dioxane (12 mL) was added 1,4-dibromobenzene (21.2 mmol, 5 g), 2-(di-t-butylphosphine)biphenyl (1.02 mmol, 304mg), potassium t-butoxide (25.5 mmol, 2.47 g) and Pd2(dba)3 (0.254 mmol, 233 mg). The mixture was degassed under a stream of nitrogen and then heated to reflux for 20 h. The mixture was diluted with EtOAc and washed with water and brine. The organic extract was concentrated under reduced pressure and the residue was chromatographed to give the desired product

  • 38
  • [ 106-37-6 ]
  • [ 6274-57-3 ]
  • 4'-bromo-N,N-dimethylbiphenylmethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; magnesium;tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; a) A solution of the Grignard reagent prepared from 344 mg of magnesium and 2.27 g of 1,4-dibromobenzene in 15 ml of THF (tetrahydrofuran) is added dropwise to a suspension of 2 g of 4-bromo-N,N-dimethylbenzylamine and 158 mg of tetrakistriphenylphosphinepalladium in 10 ml of THF. The addition is carried out at room temperature and under an argon atmosphere. After completion of the addition, the mixture is heated to boiling for an additional 5 hours and then evaporated under reduced pressure. The residue is then treated with ether and saturated ammonium chloride solution and the aqueous phase is separated. This is extracted with ether. The organic extracts are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated. The residue is purified by chromatography on silica gel while eluding with methylene chloride/methanol 9:1. 4'-Bromo-N,N-dimethylbiphenylmethanamine, m.p. 60-62 C., is obtained.
  • 39
  • [ 7758-89-6 ]
  • [ 112-29-8 ]
  • [ 106-37-6 ]
  • [ 106418-67-1 ]
YieldReaction ConditionsOperation in experiment
With N,N,N,N,-tetramethylethylenediamine; iodine; In tetrahydrofuran; nitrogen; benzene; 1 Synthesis of 4-Decylbromobenzene: In a reaction flask were charged 10.2 g of metallic magnesium, 100 ml of THF, and a small amount of iodine in a nitrogen stream, and a part of 500 ml of a THF solution containing 100 g of 1,4-dibromobenzene was added thereto dropwise to initiate reaction. Then, the rest of the solution was added dropwise at 25 to 30 C. over a 2-hour period, and the mixture was allowed to react at 40 C. for 1 hour, followed by cooling to prepare a Grignard reagent. Separately, 187 g of decyl bromide, 500 ml of benzene, 98.3 g of N,N,N',N'-tetramethylethylenediamine, and 2.1 g of copper (I) chloride were put in a reaction flask, and the atmosphere was displaced with nitrogen. The mixture was heated to 50 C., and the above prepared Grignard reagent was added thereto dropwise at that temperature over 30 minutes. The reaction mixture was allowed to react for 24 hours, cooled, and poured into a saturated aqueous ammonium solution, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate to recover 107 g of a crude product. The crude product was distilled in a Claisen flask equipped with a Vigreaux tube cylinder to obtain 43.7 g of the title compound.
  • 40
  • [ 106-37-6 ]
  • [ 82832-73-3 ]
  • 1,4-bis[4-(trans-4-propylcyclohexyl)-cyclohexen-1-yl]benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium hydrogen sulphate; In tetrahydrofuran; nitrogen; toluene; EXAMPLE 26 Preparation of 1,4-bis[4-(trans-4-propylcyclohexyl)-cyclohexen-1-yl]benzene (a compound of the formula (X) wherein R is propyl) A solution of p-dibromobenzene (5.6 g, 0.024 mol) dissolved in tetrahydrofuran (200 ml) was dropwise added to sliced Mg (1.2 g, 0.049 mol) in nitrogen current so as to give soft reflux. After 7 hours, the reaction finished to yield its magnesium bromide, to which a solution of <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)-cyclohexanone</strong> (10.9 g, 0.049 mol) dissolved in tetrahydrofuran (100 ml) was rapidly dropwise added while the temperature was kept at 30 C. or lower. After the addition, the mixture was refluxed for 1.5 hour and 3N hydrochloric acid was added. The reaction liquid was extracted with toluene (100 ml*3), combined toluene layers were washed with water and the solvent was distilled off under reduced pressure. The remaining oily substance was 1,4-bis[4-(trans-4-propylcyclohexyl)-cyclohexan-1-ol]benzene, to which potassium hydrogen sulfate (2.5 g) was added, followed by dehydrating at 200 C. for 2 hours in nitrogen current, cooling, adding toluene (300 ml), filtering off potassium hydrogen sulfate, washing toluene layer with water, distilling off the solvent under reduced pressure and recrystallizing the residue from toluene to obtain an objective product, 1,4-bis[4-(trans-4-propylcyclohexyl)cyclohexen-1-yl]benzene (yield: 0.9 g) having a C-Sm point of 98.5 C. and a Sm-I point of 300 C. or higher.
  • 41
  • [ 426219-51-4 ]
  • [ 106-37-6 ]
  • [ 426219-57-0 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; In hexane; (i) Production of 8-(4-bromophenyl)-5,6,7,8-tetrahydroimidazo-[1,5-a]pyridin-8-ol The reactions in the same manner as in Example 19 using 1,4-dibromobenzene (4.53 g), a hexane solution (1.6 M; 10.0 ml) of n-butyl lithium and <strong>[426219-51-4]6,7-dihydroimidazo[1,5-a]pyridin-8(5H)-one</strong> (1.09 g) afforded the title compound (916 mg) as a pale-yellow powder. 1H-NMR(CDCl3) delta: 1.85-2.05(2H, m), 2.1-2.25(1H, m), 2.3-2.5(1H, m), 3.85-4.05(1H, m), 4.15-4.3(1H, m), 6.67(1H, s), 7.36(2H, d, J=8.8 Hz), 7.46(2H, d, J=8.8 Hz), 7.47(1H, s). IR(KBr): 1485, 1453, 1397, 1208, 1105, 953, 936, 831, 812 cm-1.
  • 42
  • [ 106-37-6 ]
  • [ 61903-11-5 ]
  • [ 1042918-53-5 ]
YieldReaction ConditionsOperation in experiment
82% With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 20 - 80℃; a) 1 -Acetyl-4-(4-bromophenyl)-[1 ,4]diazepan <n="64"/>To a solution of 1 ,4-dibromobenzene (3.30 g, 14 mmol) in toluene (44 ml_) under Ar-atmosphere, sodium te/t-butoxide (1.88 g, 19.60 mol), BINAP (0.17 g, 0.28 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol) and 1-acetylhomopiperazine (2 g, 14 mmol) were added at room temperature. The reaction mixture was heated at 80 C overnight. The resulting mixture was cooled, diluted with MeOH and filtered over CeI ite. The filtrate was concentrated to dryness. The crude product obtained was chromatographed over silica gel using Hexane/EtOAc mixtures of increasing polarity as eluent, to afford 3.42 g of the desired compound (82% yield). LC-MS (method 1 ): tR = 7.08 min; m/z = 299 (MH+).
  • 43
  • [ 106-37-6 ]
  • [ 932-35-4 ]
  • [ 910649-26-2 ]
YieldReaction ConditionsOperation in experiment
35% Preparation 1 (4-bromophenyl)(3-hydroxy-2-pyridinyl)methanone 48.5 g (205.5 mM) of 1,4-dibromobenzene are added dropwise to a mixture containing one crystal of iodine and 5 g (205.5 mM) of magnesium metal covered with 150 ml of THF. The mixture is stirred at the reflux temperature of the solvent for 2 hours and then cooled to 10 C. 12.34 g (102.7 mM) of 2-cyano-3-pyridinol are then added dropwise. The reaction medium is heated at the reflux temperature of the solvent for 3 hours, then stirred for 18 h at room temperature and then treated with 300 ml of 0.5 N sulfuric acid. The solvents are driven off under reduced pressure and the residual aqueous phase is brought to pH 4 by adding a necessary and sufficient amount of 2 N sodium hydroxide solution. The neutralized mixture is extracted with dichloromethane and the organic phase is dried over magnesium sulfate. After evaporation of the solvent, the expected product is obtained in the form of a yellow solid with a yield of 35%. M.p.=94-95 C.
  • 44
  • [ 106-37-6 ]
  • [ 374564-35-9 ]
  • 46
  • [ 106-37-6 ]
  • [ 195602-17-6 ]
  • [ 1160930-68-6 ]
  • 47
  • [ 106-37-6 ]
  • [ 250275-15-1 ]
  • [ 1173179-67-3 ]
  • 49
  • [ 103012-26-6 ]
  • [ 106-37-6 ]
  • 9-(4-bromophenyl)-3-phenyl-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% In a 500 mL three neck flask were put 8.0 g (34 mmol) of 1,4-dibromobenzene, 7.0 g (28 mmol) of <strong>[103012-26-6]<strong>[103012-26-6]3-phenyl-9H-carbazol</strong>e</strong>, and 0.27 g (1.0 mmol) of 18-crown-6-ether. This mixture was stirred while being heated at about 130 C., so that 1,4-dibromobenzene was melted. After that, to this mixture were added 3.0 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), 9.5 g (69 mmol) of potassium carbonate, and 0.20 g (1.0 mmol) of copper(I) iodide, followed by stirring at 170 C. for 3 hours. Then, this mixture was cooled to about 110 C. Next, 100 mL of toluene was added to this mixture, which was cooled to room temperature.This mixture was suction filtered. The resulting filtrate was washed with dilute hydrochloric acid three times, with a saturated aqueous sodium hydrogen carbonate solution three times, and with saturated brine once. Then, the mixture was separated into an aqueous layer and an organic layer. The organic layer was dried with magnesium sulfate, and this mixture was gravity filtered. An oily substance obtained by concentration of the resulting filtrate was purified by silica gel column chromatography (the developing solvent was a mixed solvent of a 7:1 ratio of hexane to toluene) to give a colorless oily substance. This oily substance was melted in a small amount of hexane. Methanol was added to this mixture, followed by irradiation with ultrasonic waves to precipitate a white solid. This solid was collected by suction filtration to give the desired substance as 2.5 g of a white powder in a yield of 22%.
  • 50
  • [ 106-37-6 ]
  • [ 181219-01-2 ]
  • [ 113682-56-7 ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 48h;Inert atmosphere; Reflux; Example 1 Synthesis of 4,4'-(1,4-phenylene)bis(1-hexylpyridin-1-ium) bis(tetrafluroborate) A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (4.34 g, 21.2 mmol), 1,4-dibromobenzene (2.00 g, 8.5 mmol), K2CO3 (2.92 g, 21.2 mmol) and Pd(PPh3)4 (0.49 g, 5 mol percent) in PhMe (30 mL) and EtOH (30 mL) under N2 was heated at reflux for 48 h. The resulting mixture was poured into water (50 mL), extracted with dichloromethane (2*100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using MeOH (0-5percent) in dichloromethane as eluent. The solvent was removed under reduced pressure and the residue crystallised from hot EtOAc/hexanes to give 1,4-di(4-pyridyl)benzene (1.52 g, 77percent) as a pale yellow powder.
71% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In N,N-dimethyl-formamide; toluene; at 130℃; for 48h;Inert atmosphere; Pyridylboronic pinacol ester (3.64 g, 17.8 mmol), 1,4-dibromobenzene (1.40 g, 5.92 mmol), and Cs2CO3 (11.6 g, 35.5 mmol) were added to a 1:1 mixture of dry PhMe/DMF (300 mL), which had been degassed with Ar for 15 min. Next, Pd(PPh3)4 (0.68 g, 0.59 mmol) was added to the reaction mixture and the solution heated to 130° C. under Ar for 48 h. Then, the reaction mixture was cooled to room temperature and the palladium catalyst filtered off using Celite. The organic phase was concentrated under vacuum and then dissolved in CH2Cl2 followed by extraction with H2O three times. The organic layer was made acidic (pH 2-3) by adding dropwise concentrated HCl, which caused the desired product to precipitate from solution. The precipitate was collected by filtration and then dissolved in H2O. Finally, aq. NaOH (10 M) was added dropwise to the water layer until the pH was 8-9, which resulted in precipitation of pure product ExBIPY (973 mg, 71percent) as a white solid. The yield of the product obtained in the reaction was 71percent. 1H NMR (500 MHz, CDCl3, ppm): deltaH 8.72 (AA? of AA?XX?, J=4.6, 1.6 Hz, 4H), 7.80 (s, 4H), 7.59 (XX? of AA?XX?, J=4.6, 1.6 Hz, 4H).
  • 51
  • [ 106-37-6 ]
  • [ 1158098-73-7 ]
  • [ 1279089-26-7 ]
YieldReaction ConditionsOperation in experiment
96% Step 2: Preparation of N-[3-(4-bromophenyl)oxetan-3-yl]-2-methylpropane-2-sulfinamide A solution of n-butyllithium in hexanes (1.65M, 4.92 mL) was added dropwise to a solution of 1,4-dibromobenzene (2.05 g) in THF (25 mL) dropwise over the course of 30 min at -78 C. The resulting mixture was stirred at the same temperature for 1 h. To the mixture was added a solution of <strong>[1158098-73-7]2-methyl-N-oxetan-3-ylidenepropane-2-sulfinamide</strong> (1.02 g) in THF (5 mL) dropwise over the course of 30 min at -78 C. The reaction mixture was stirred for an additional 30 min. at -78 C. then allowed to warm to room temperature. After being stirred for 1 h at room temperature, the reaction mixture was quenched by addition of saturated ammonium chloride aqueous solution. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated sodium bicarbonate solution then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (50-100% ethyl acetate in hexanes then 5% methanol in ethyl acetate) gave the product (1.85 g, 96%). 1HNMR (CDCl3) 400 MHz delta: 7.55 (d, J=8.7 Hz, 2H), 7.27 (d, J=8.7 Hz, 2H), 5.16 (d, J=6.9 Hz, 1H), 5.06 (d, J=6.9 Hz, 1H), 5.02 (d, J=6.9 Hz, 1H), 4.94 (d, J=6.9 Hz, 1H), 4.05 (br s, 1H), 1.22 (s, 9H). LCMS: 332, 334 [M+H].
76% p-Dibromobenzene (0.8 g, 3 mmol) was dissolved in tetrahydrofuran (30 mL).Add n-butyl lithium (3 mL, 3 mmol),After stirring at -80 C for 1 hour,Add tert-butylsulfinyl-3-oxetanimide (0.6 g, 3 mmol),Stir at room temperature for 2 hours.The reaction solution was concentrated to dryness.Purified by silica gel column chromatography,A white solid (0.6 g, 76%) was obtained.
36% Step 1: Preparation of N-(3-(4-bromophenyl)oxetan-3-yl)-2-methylpropane-2-sulfinamide To 1,4-dibromobenzene (0.5 g, 2.12 mmol) in dry THF (8.8 mL) at -78 C. was added a solution of n-butyllithium (1.2 mL, 2.97 mmol). The resulting mixture was stirred for 1 h, then <strong>[1158098-73-7]2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide</strong> (0.371 g, 2.12 mmol) in dry THF (1.8 mL) was added dropwise. The reaction was allowed to warm to ambient temperature and stirred another 1 h. The mixture was then quenched with saturated NH4Cl (aq) and extracted with EtOAc. The organic phase was washed with saturated sodium bicarbonate (aq), dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by column chromatography (gradient 0-100% EtOAc in heptane) to afford N-(3-(4-bromophenyl)oxetan-3-yl)-2-methylpropane-2-sulfinamide (284 mg, 36%): LCMS Rt=0.95 min (condition B), MS (M+3)=334.0.
  • 52
  • [ 374564-35-9 ]
  • [ 106-37-6 ]
YieldReaction ConditionsOperation in experiment
99% With pyridinium hydrobromide perbromide; In tetrahydrofuran; water; at 20℃; for 0.333333h; General procedure: The trifluoroborate (1.0 mmol) was dissolved in (1:1 v/v) mixture of tetrahydrofuran and water (10 mL). Pyridinium tribromide (or tetrabutylammonium tribromide) (1.0 mmol) was added to this solution. The mixture was stirred for the appropriate time and temperature (Tables 1and 2) and then diluted with 10 mL of ether. The aqueous layer was extracted twice with ether (5 mL) and the combined organic phase was dried over anhydrous Na2SO4. After evaporation of the solvent the residue was purified by silica gel column chromatography [elute: hexane (or pentane)-ethyl acetate (or Et2O)].
  • 53
  • [ 106-37-6 ]
  • [ 1864-94-4 ]
  • [ 1539-04-4 ]
  • 54
  • [ 106-37-6 ]
  • [ 68-12-2 ]
  • [ 74553-29-0 ]
  • 55
  • [ 944392-68-1 ]
  • [ 106-37-6 ]
  • [ 1415325-73-3 ]
  • 56
  • [ 109-72-8 ]
  • [ 106-37-6 ]
  • [ 2162-74-5 ]
  • [ 7270-42-0 ]
  • [ 1229182-31-3 ]
  • 57
  • [ 25475-67-6 ]
  • [ 106-37-6 ]
  • [ 1370708-45-4 ]
YieldReaction ConditionsOperation in experiment
80% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 8h;Inert atmosphere; General procedure: A round-bottomed flask was charged with Pd2(dba)3 (5 mol percent ), ligand (10 molpercent), aryl halide (1mmol), appropriate isoquinolinamine (1 mmol), base (1.5 mmol) and dry solvent (5 mL). Theflask was flushed with argon for 5 min. The mixture was heated at reflux under magnetic stirring.After cooling down to room temperature, the reaction mixture was concentrated and the residuewas purified by flash column chromatography on silica gel.
  • 58
  • [ 106-37-6 ]
  • [ 71616-83-6 ]
  • 59
  • [ 106-37-6 ]
  • [ 5720-05-8 ]
  • [ 149104-90-5 ]
  • [ 613-33-2 ]
  • [ 50670-49-0 ]
  • [ 5731-01-1 ]
  • [ 787-69-9 ]
  • [ 5748-38-9 ]
  • 60
  • [ 106-37-6 ]
  • [ 1692-15-5 ]
  • [ 39795-60-3 ]
YieldReaction ConditionsOperation in experiment
61% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110℃; for 48h;Inert atmosphere; In the Ar gas protection,Using the intermediate H as a starting material (620 mg; 5 mmol)Were charged into a 50 ml two-necked flask,1,4-dibromobenzene(1.2 g; 5 mmol), 10 mg of Pd (pph3) 4, anhydrous potassium carbonate (1.38 g, 5 mmol)5ml distilled oxygen,40ml anhydrous oxygen-free toluene,110 ° C reflux reaction 48h.Saturated ammonium chloride solution was quenched and extracted with ethyl acetate.The solvent was removed by rotary evaporator,The crude product was then purified by column chromatography to give the substituent (11) as a white solid 700mg(61percent).
26.26% A 500 mL sealed tube was charged with pyridin-4-ylboronic acid (1.6 g, 13.0 mmol) 1,4-dibromobenzene (3.07 g, 13.0 mmol), sodium carbonate (5 mL, 2M solution) and mixture of toluene (10 mL) and water (10 mL). The reaction mixture was purged with argon for 30 mm. Then, Pd(PPh3)4 (0.75 g, 0.05 eq) was added to the reactionmixture and the said mixture was heated at 90 00 for about 12 h. After cooling, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na2SO4. The organic layer was concentrated under vacuo to yield crude product, which was purified by column chromatography to yield title compound (0.8 g, 26.26percent) as a white solid. LCMS: (M+2) = 236.0; 1H NMR:(DMSO-d6, 300MHz) 68.64-8.66 (d, 2H), 7.71- 7.80 (m, 6H).
26.26% A 500 mL sealed tube was charged with pyridin-4-ylboronic acid (1.6 g, 13.0 mmol)1 ,4-dibromobenzene (3.07 g, 13.0 mmol), sodium carbonate (5 mL, 2M solution) andmixture of toluene (10 mL) and water (10 mL). The reaction mixture was purged withargon for 30 mm. Then, Pd(PPh3)4 (0.75 g, 0.05 eq) was added to the reactionmixture and heated at 90 00 about 12 h. After cooling, the reaction mixture wasextracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na2SO4. The organic layer was concentrated under vacuo to yield crude product, which was purified by column chromatography to yield title compound (0.8 g, 26.26percent) as a white solid. LCMS: (M+2) = 236.0; 1H NMR: (DMSO-d6, 300MHz ) 68.64-8.66 (d, 2H), 7.71- 7.80 (m, 6H).
With potassium carbonate; palladium; In toluene; at 80℃; for 16h;Inert atmosphere; Under N2 gas purification system, Compound A, 0.9 equivalents of compound B, 0.05 equivalents of Pd (0) and 4.0 equivalents of potassium carbonate into toluene, the mixture at a temperature of 80 deg. C oil bath with stirring. After 16 hours, water was added to the mixture, was extracted, the product was eluted with methylene chloride and hexane (2: 1) through the column to obtain a white solid compound C.

  • 61
  • [ 110-86-1 ]
  • [ 106-37-6 ]
  • [ 39795-60-3 ]
  • 62
  • [ 106-37-6 ]
  • [ 173186-91-9 ]
  • 1-benzyl-4-(4-bromo-phenyl)-3,3-dimethyl-piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
STEP B: 1-Benzyl-4-(4-bromo-phenyl)-3,3-dimethyl-piperidin-4-ol1,4-Dibromobenzene (9.31 g, 39.5 mmol) was dissolved in dry THF (50 ml) in a two necks round-bottom flask equipped with a stirring bar, a septum, and an addition funnel with nitrogen inlet. The solution was cooled to -78C, and n-BuLi (1.6 M, 24.7 ml, 39.5 mmol) was added dropwise via syringe. The 25 resulting milky suspension was stirred for 1 hour at the same temperature, before a solution of <strong>[173186-91-9]1-benzyl-3,3-dimethyl-piperidin-4-one</strong> (7.15 g, 32.9 mmol) in THF (50 ml) was slowly added from the addition funnel. The clear solution was then stirred for 3 hours allowing the temperature to rise to ambient. The reaction was quenched with saturated NH4Cl (50 ml) and water (100 ml). The organics were extracted with ethyl acetate (100 ml). The organic layer was washed with brine (50 ml), dried over MgSO4, filtered and concentrated to a viscous oil. Purification of the oil over silica gel eluting with a gradient of MeOH in DCM from 0 to 6% yielded the desired product. 1H NMR (300 MHz, CDCl3) ppm 0.72 (s, 3 H), 0.94 (s, 3 H), 1.41 - 1.55 (m, 2 H), 2.29 (d, J=11.2 Hz, 1 H), 2.38 (d, J=11.2 Hz, 1 H), 2.48 (m, 1 H), 2.74 - 2.86 (m, 2 H), 3.47 (d, J=13.4 Hz, 1 H), 3.59 (d, J=13.4 Hz, 1 H), 7.22 - 7.39 (m, 7 H), 7.44 (d, J=8.7 Hz, 2H). MS m/z 374 (M+H)+
  • 64
  • [ 106-37-6 ]
  • [ 134150-01-9 ]
  • [ 123560-45-2 ]
YieldReaction ConditionsOperation in experiment
94% With potassium phosphate monohydrate; palladium dichloride; 3-(diphenylphosphino)propionic acid; In dimethyl sulfoxide; at 100℃; for 12h;Schlenk technique; General procedure: The Schlenk tube (5 mL) equipped with a stir bar was charged with PdCl2 (1.0 mol%), Ph2P(CH2)2COOH (2.0 mol%), and K3PO4 ·H2O (4.0 equiv.), then 1,4-dibromobenzene (0.5 mmol), phenylboronic acid (1.20 mmol), and DMSO (2.0 ml) were added, and the mixture was stirred at 100 C until the substrate was completely consumed. After cooling to room temperature, the solution was quenched with water and extracted with EtOAc (3 × 10 mL). The combined EtOAc extracts were dried over anhydrous Na2SO4 and filtrated and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE as the eluent to obtain the desired products.
  • 65
  • [ 106-37-6 ]
  • [ 501-65-5 ]
  • [ 486-52-2 ]
  • 66
  • [ 106-37-6 ]
  • C8H7BNO4S [ No CAS ]
  • [ 364794-79-6 ]
  • 4-((4'-(thiophen-2-yl)-[1,1'-biphenyl]-3-yl)methyl)morpholine [ No CAS ]
  • 67
  • [ 426-65-3 ]
  • [ 106-37-6 ]
  • 1-(4-bromophenyl)-2,2,3,3,3-pentafluoropropan-1-one [ No CAS ]
  • 68
  • [ 106-37-6 ]
  • [ 121219-12-3 ]
  • [ 136423-73-9 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate monohydrate; palladium dichloride; 3-(diphenylphosphino)propionic acid; In dimethyl sulfoxide; at 100℃; for 12h;Schlenk technique; General procedure: The Schlenk tube (5 mL) equipped with a stir bar was charged with PdCl2 (1.0 molpercent), Ph2P(CH2)2COOH (2.0 molpercent), and K3PO4 ·H2O (4.0 equiv.), then 1,4-dibromobenzene (0.5 mmol), phenylboronic acid (1.20 mmol), and DMSO (2.0 ml) were added, and the mixture was stirred at 100 °C until the substrate was completely consumed. After cooling to room temperature, the solution was quenched with water and extracted with EtOAc (3 × 10 mL). The combined EtOAc extracts were dried over anhydrous Na2SO4 and filtrated and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE as the eluent to obtain the desired products.
  • 69
  • [ 106-37-6 ]
  • [ 33228-45-4 ]
  • N1,N4-bis(4-hexylphenyl)benzene-1,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; Example 1-5 Preparation of N1,N4-bis(4-hexylphenyl)benzene-1,4-diamine 1,4-Dibromobenzene (0.5 g, 2.1 mmol) was dissolved in 1,4-dioxane, mixed with <strong>[33228-45-4]4-hexylaniline</strong> (0.88 mL, 4.5 mmol), Pd2(dba)3 (0.061 mg, 0.1 mmol), XPhos (0.1 g, 0.21 mmol) and t-BuONa (0.6 g, 6.4 mmol) and then heated at 100 C. for 18 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and water was added. The mixture was extracted with MC, dried with Na2SO4, concentrated and suspended in MeOH to obtain the target compound (0.68 g, yield: 75%) (compound 1e). 1H NMR (400 MHz, CDCl3): delta 7.065-7.044 (d, 4H), 7.006 (s, 4H), 6.925-6.905 (d, 2H), 5.464 (s, 2H), 2.555-2.516 (t, 4H), 1.600-1.547 (m, 4H), 1.312-1.308 (m, 12H), 0.905-0.872 (t, 6H).
  • 71
  • [ 864377-33-3 ]
  • [ 106-37-6 ]
  • 9-(4'-bromo-[1,1'-biphenyl]-3-yl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 40 - 100℃; for 5h;Inert atmosphere; Under a stream of nitrogen 50.0 g (187.18 mmol) of (3 - (9H-carbazol-9-yl) phenyl) boronic acid, 47.53 g (187.18mmol) of 1,4-dibromobenzene, 77.61 g (561.55 mmol) of K2CO3, 1000 ml / 250 ml / stirred into the Toluene / H2O / EtOH in 250 ml. At 40°C into the Pd (PPh3) 4 g of 10.81 (5 molpercent) it was stirred at 100°C for 5 hours. After completion of the reaction and extracted with methylene chloride and the filter insert MgSO4. The solvent of the filtered organic layer was purified by column chromatography to 57.41 g (yield: 77percent) of 9- (4'-bromo- [1,1'-biphenyl] -3-yl) -9H-carbazole was obtained.
  • 72
  • [ 100124-06-9 ]
  • [ 106-37-6 ]
  • [ 955959-84-9 ]
YieldReaction ConditionsOperation in experiment
13.7 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 80℃; for 5h; At 80C, 4-dibenzofuranboronic acid (13.3g), 1,4-dibromobenzene (10g), tetrakis(triphenylphosphine)palladium (3.02g), toluene (158mL), ethanol (65mL), water (65mL), and potassium carbonate (21.69g) were stirred for 5 hours. The reaction was monitored by thin layer chromatography. Upon completion of the reaction, it was quenched with water (100mL) and extracted with ethyl acetate (100mL). The organic layer was extracted with water (3x30mL) and dried over anhydrous sodium sulfate. The ethyl acetate layer was collected through Celite and further purified by column chromatography. Following this, the ethyl acetate layer was evaporated to dryness under vacuum rotavap to yield 13.7g 4-(4'-bromophenyl)dibenzofuran.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; at 80℃; for 24h;Inert atmosphere; Under nitrogen environment, compound G was dissolved in tetrahydrofuran / toluene (5: 1) and then 0.9 equivalent of compound F was added. After 4.4 equivalent of Potassium carbonate was dissolved in DI water, 0.05 equivalent of Pd (0) was added. The reaction mixture was then refluxed at 80 C. for 24 hours and the reaction was terminated. After extraction with organic solvent, the organic solvent was removed. Compound H was obtained by reprecipitation after a column.
  • 73
  • [ 106-37-6 ]
  • [ 13315-17-8 ]
  • 74
  • [ 106-37-6 ]
  • [ 221874-51-7 ]
  • tert-butyl (R)-(1-(4-bromophenyl)-2-oxopiperidin-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With potassium phosphate; copper(l) iodide; N,N-dimethylethylenediamine; In 1,4-dioxane; at 60℃;Sealed tube; Inert atmosphere; In a 1 L sealed tube, to a solution of <strong>[221874-51-7](R)-tert-butyl (2-oxopiperidin-3-yl)carbamate</strong> (23 g, 110 mmol) in 1,4-dioxane (300 mL) was added 1,4-dibromobenzene (28 g, 120 mmol), potassium phosphate tribasic (34 g, 160 mmol), cuprous iodide (8.2 g, 43 mmol), Nu,Nu'- dimethylethylenediamine (4.7 ml, 43 mmol). The reaction mixture was purged with Argon for 10-15 minutes and then heated to 60 C for overnight. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with brine solution (200 mL). The organic layer was dried over Na2S04 and concentrated to produce the crude product. The crude compound was purified through 330 gm Silica column and was eluted with ethylacetate:pet-ether (40:60) to achieve off white solids of tert-butyl (l-(4- bromophenyl)-2-oxopiperidin-3-yl)carbamate (20 gm). Chiral SFC analysis of the purified product showed -10% epimerization. The compound was then purified via SFC to afford Intermeidate la (15 gm, 40 mmol, 38% yield) as a white solid. MS(ESI) m/z: 369.0/371.0 (M+H). NMR (400 MHz, CDCh): delta ppm 7.48 (d, J = 4.8 Hz, 2H), 7.11 (d, J= 4.8 Hz, 2H), 5.48 (br-s, 1H), 4.25-4.18 (m, 1H), 3.70-3.62 (m, 2H), 2.60-2.52 (m, 1H), 2.08-1.95 (m, 2H), 1.74-1.64 (m, 1H), 1.43 (s, 9H). [a]D25 (c = 0.1, MeOH): +30.0. Chiral Purity (SFC): 99.9%, retention time = 4.15 min (time of Peak-01 (0.105%) = 3.03 min & Retention time of Peak-02 (99.9%) = 4.15 min; Co-Solvent: 0.2%DEA in Methanol; Column: Whelk-01 ( R,R )(250 X 4.6)mm 5u; Column Temperature: 24.5; Total Flow: 3; C02 Flow Rate: 1.8; Co-Solvent Flow Rate: 1.2; Co-Solvent% 40; Back Pressure 100.) Preparative SFC Conditions: Column/dimensions: Whelk(R,R) (250 X 30) mm, 5u; C02%: 70%; Co-solvent%: 30% of (0.2% DEA in methanol); Total Flow: 120 g /min; Back Pressure: 100 bar; Temperature: 30C; UV: 240 nm. Retention time of Peak-01 = 3.20 min & Retention time of Peak-02 = 4.60 min;
38% With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 60℃;Sealed tube; Inert atmosphere; In a 1 L sealed tube, to a solution of <strong>[221874-51-7](R)-tert-butyl (2-oxopiperidin-3-yl)carbamate</strong> (23 g, 110 mmol) in 1,4-dioxane (300 mL) was added 1,4-dibromobenzene (28 g, 120 mmol), potassium phosphate tribasic (34 g, 160 mmol), cuprous iodide (8.2 g, 43 mmol), Nu,Nu'- dimethylethylenediamine (4.7 ml, 43 mmol). The reaction mixture was purged with Argon for 10-15 minutes and then heated to 60 C for overnight. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with brine solution (200 mL). The organic layer was dried over Na2S04 and concentrated to produce the crude product. The crude compound was purified through 330 g Silica column and was eluted with ethylacetate:pet-ether (40:60) to achieve off white solids of tert-butyl (l-(4- bromophenyl)-2-oxopiperidin-3-yl)carbamate (20 g). Chiral SFC analysis of the purified product showed -10% epimerization. The compound was then purified via SFC to afford Intermediate 1 (15 g, 40 mmol, 38% yield) as a white solid. MS(ESI) m/z: 369.0/371.0 (M+H). NMR (400 MHz, CDCh):? ppm 7.48 (d, J = 4.8 Hz, 2H), 7.11 (d, J= 4.8 Hz, 2H), 5.48 (br-s, 1H), 4.25-4.18 (m, 1H), 3.70-3.62 (m, 2H), 2.60-2.52 (m, 1H), 2.08- 1.95 (m, 2H), 1.74-1.64 (m, 1H), 1.43 (s, 9H). [a]D25 (c = 0.1, MeOH): +30.0. Chiral Purity (SFC): 99.9%, retention time = 4.15 min (time of Peak-01 (0.105%) = 3.03 min & Retention time of Peak-02 (99.9%) = 4.15 min; Co-Solvent: 0.2%DEA in Methanol; Column: Whelk-01 ( R,R )(250 X 4.6)mm 5u; Column Temperature: 24.5; Total Flow: 3; C02 Flow Rate: 1.8; Co-Solvent Flow Rate: 1.2; Co-Solvent% 40; Back Pressure 100.) (0145) Preparative SFC Conditions: Column/dimensions: Whelk(R,R) (250 X 30) mm, 5u; C02%: 70%; Co-solvent%: 30% of (0.2% DEA in methanol); Total Flow: 120 g /min; Back Pressure: 100 bar; Temperature: 30C; UV: 240 nm. Retention time of Peak-01 = 3.20 min & Retention time of Peak-02 = 4.60 min.
38% With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 60℃;Inert atmosphere; In a 1 L sealed tube, to a solution of (i?)-tert-butyl (2-oxopiperidin-3-yl)carbamate (23 g, 110 mmol) in 1,4-dioxane (300 mL) was added 1,4-dibromobenzene (28 g, 120 mmol), potassium phosphate tribasic (34 g, 160 mmol), cuprous iodide (8.2 g, 43 mmol), Nu,Nu'- dimethylethylenediamine (4.7 ml, 43 mmol). The reaction mixture was purged with Argon for 10-15 minutes and then heated to 60 C for overnight. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with brine solution (200 mL). The organic layer was dried over Na2S04 and concentrated to produce the crude product. The crude compound was purified through 330 gm Silica column and was eluted with ethylacetate:pet-ether (40:60) to achieve off white solids of tert-butyl (l-(4- bromophenyl)-2-oxopiperidin-3-yl)carbamate (20 gm). Chiral SFC analysis of the purified product showed -10% epimerization. The compound was then purified via SFC to afford Intermeidate la (15 gm, 40 mmol, 38% yield) as a white solid. MS(ESI) m/z: 369.0/371.0 (M+H). NMR (400 MHz, CDCh): delta ppm 7.48 (d, J= 4.8 Hz, 2H), 7.11 (d, J= 4.8 Hz, 2H), 5.48 (br-s, 1H), 4.25-4.18 (m, 1H), 3.70-3.62 (m, 2H), 2.60-2.52 (m, 1H), 2.08-1.95 (m, 2H), 1.74-1.64 (m, 1H), 1.43 (s, 9H). [a]D25 (c = 0.1, MeOH): +30.0. Chiral Purity (SFC): 99.9%, retention time = 4.15 min (time of Peak-01 (0.105%) = 3.03 min & Retention time of Peak-02 (99.9%) = 4.15 min; Co-Solvent: 0.2%DEA in (0236) Methanol; Column: Whelk-01 ( R,R )(250 X 4.6)mm 5u; Column Temperature: 24.5; Total Flow: 3; C02 Flow Rate: 1.8; Co-Solvent Flow Rate: 1.2; Co-Solvent% 40; Back Pressure 100.) (0237) Preparative SFC Conditions: Column/dimensions: Whelk(R,R) (250 X 30) mm, 5u; (0238) C02%: 70%; Co-solvent%: 30% of (0.2% DEA in methanol); Total Flow: 120 g /min; Back Pressure: 100 bar; Temperature: 30C; UV: 240 nm. Retention time of Peak-01 = 3.20 min & Retention time of Peak-02 = 4.60 min;
  • 76
  • [ 5447-86-9 ]
  • [ 106-37-6 ]
  • C22H19BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% 250 ml of a four-necked flask, and 11.8 g was added under an atmosphere of nitrogen gas1,4-dibromobenzene (0.05 mol) and1.33 g Mg powder (0.055 mol), 60 ml of tetrahydrofuran,Heated to reflux for 4 hours, the reaction is complete, the formation of format reagents;11.1 g of <strong>[5447-86-9]10,10-dimethylanthrone</strong> (0.05 mol) was dissolved in 50 ml of tetrahydrofuran,The above-mentioned format reagent was added dropwise and reacted at 60 C for 24 hours to form a large amount of white precipitate,Finally, saturated NHCl4 was added to convert the format salt to alcohol. After completion of the reaction, the ether was extracted,Drying and steaming, petroleum ether: dichloromethane mixed solvent (3: 2) silica gel column,A slightly solid solid tertiary alcohol (yield 88%) was obtained
  • 77
  • [ 106-37-6 ]
  • [ 146553-06-2 ]
  • (S)-tert-butyl (1-(4-bromophenyl)-1-oxopropan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% A solution of 1,4-dibromobenzene 219 (6.00 g, 25.4 rnmol) in dry THF (40 mL) was cooled to -78 C under nitrogen atmosphere. To the solution was added n-BuLi (2.5 M, 10.3 mL, 25.8 mmol) slowly and the reaction mixture was stirred at same temperature for 45 min., white precipitation was formed during the period. A solution of (S)-tert-butyl(1-(methoxy(methyl)-amino)-1-oxopropan-2-yl)carbamate 218 ( 1.50 g, 6.46 mmol) in THF (20 mL) was added to the reaction mixture slowly, the reaction mixture was stirred at same temperature for another 2 h before it was quenched with saturated NH4Cl solution (50 mL). The aqueous layer was extracted with EtOAc (100 mL) and the organic layer was concentrated and the crude was purified by combi-flash companion (silica gel, 10% EtOAc/hexanes) to give (S)-tert-butyl (1-(4-bromophenyl)-1-oxopropan-2-yl)carbamate 220 (320 mg, 15%). lH NMR (400 MHz, DMSO-d6): delta 7.88 (d, J = 8.4 Hz, II I). 7.73 (d, J= 8,4 Hz, 2H), 7.37 (d, J = 7.2 Hz, 1H), 4.99-4.96 (m, 1H), 1 ,33 (s, 9H), 1 ,2.1 (d, J= 6.8 Hz, 3H)
  • 78
  • [ 2039-82-9 ]
  • [ 106-37-6 ]
  • [ 18869-30-2 ]
YieldReaction ConditionsOperation in experiment
93% With trans-di(mu-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); sodium acetate; In N,N-dimethyl acetamide; at 100 - 140℃; for 48h;Schlenk technique; Inert atmosphere; General procedure: A solution of aryl halide 7a-c (6.37mmol; 1equiv) anddry NaOAc (7.64mmol; 1.2equiv) in N,N-dimethylacetamide (3mL) was placed in a Schlenk tube and repeatedly degassed and purged with argon five times. The styrene derivative 6a-d (1.4equiv) was added and the mixture was heated to 100C. Next, a solution of Herrmann's catalyst (59.68mg, 1mol%) in N,N-dimethylacetamide (2mL) was added and the mixture was heated to 140C during 48h. The product was worked up by addition of H2O and the organic phase was extracted with EtOAc (3×30mL). The combined organic phases were dried over MgSO4. After removal of the solvent, the residue was purified by silica gel column chromatography with cyclohexane/EtOAc (98:02) as the eluent.
  • 79
  • [ 106-37-6 ]
  • [ 106-94-5 ]
  • [ 588-93-2 ]
YieldReaction ConditionsOperation in experiment
90.5% With iron(III)-acetylacetonate; magnesium; zinc(II) chloride; In tetrahydrofuran; at 40 - 60℃; for 8h;Inert atmosphere; General procedure: Under a nitrogen atmosphere, to a two-liter three-necked flask was added 236 g of p-dibromobenzene, 185 g of 1-bromopropane and 1 liter of anhydrous tetrahydrofuran; followed by addition of 204 g of zinc chloride, 36 g of magnesium powder and 18 Grams of acetylacetone iron. The mixture was heated to about 40 °C under stirring, the reaction was initiated after a few minutes, the reaction temperature was controlled at not more than 60 °C for 8 hours. The reaction mixture was then cooled to room temperature and quenched by stirring with 200 ml of water. The tetrahydrofuran solvent was recovered by distillation and the residue was diluted with 500 ml of toluene. The toluene layer was separated and washed twice with 200 ml of saturated brine and dried over anhydrous sodium sulfate Drying, filtration, filtrate recovery of toluene recovery, and then vacuum distillation, collecting at 94-97 °C / 10 mmHg to give 170 g of p-bromopyrophenyl. The yield was 85percent.
  • 80
  • [ 106-37-6 ]
  • [ 1158098-73-7 ]
  • [ 1279089-24-5 ]
  • 81
  • [ 106-37-6 ]
  • [ 203314-28-7 ]
  • 82
  • [ 72287-26-4 ]
  • [ 106-37-6 ]
  • 4-amino-3-bromo-5-chloropyridine [ No CAS ]
  • 3-(4-bromophenyl)-5-chloropyridin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; Step 2: 3-(4-bromophenyl)-5-chloropyridin-4-amine A mixture of 3-bromo-5-chloropyridin-4-amine (5 g, 24.10 mmol), bis(pinacolato)diboron (12 g, 48320 mmol), potassium acetate (4.7 g, 48.20 mmol) and 1,1'-bis(diphenylphosphino)ferrocene palladium(II)dichloride (3.5 g, 4.82 mmol) in dioxane (100 ml) was stirred at 90° C. overnight under nitrogen. TLC showed the reaction was complete. To this mixture solution was added 1,4-dibromobenzene (11.4 g, 48.20 mmol), potassium carbonate (6.7 g, 48.20 mmol) and water (30 ml). tetrakis(triphenylphosphine)palladium (1.4 g, 1.21 mmol) was added and the mixture was stirred at 90° C. overnight under nitrogen. The reaction mixture was filtered and the filtrate was partitioned between ethyl acetate (100 ml) and water (100 ml), the organic layer was washed with brine (20 ml*2), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude residue which was purified by silica gel flash chromatography (eluted with 20-50percent ethyl acetate in hexane) to afford 3-(4-bromophenyl)-5-chloropyridin-4-amine (2.3 g, yield 34percent) as yellow solid.
  • 84
  • [ 106-37-6 ]
  • [ 932-35-4 ]
  • [ 910649-27-3 ]
  • 85
  • [ 1003846-21-6 ]
  • [ 106-37-6 ]
  • C22H26N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); In toluene; at 110℃; for 48h;Inert atmosphere; Sealed tube; Synthesis of H2bdp Derivatives. (0115) The ligand 1,4-benzenedipyrazole (H2bdp) was synthesized according to a previously reported procedure. The functionalized dibromobenzene analogues used were 1,4-dibromo-2-fluorobenzene, 1,4-dibromo-2,5-difluorobenzene, 1,4-dibromo-2,3-difluorobenzene, 1,4-dibromobenzene-d4, or 1,4-dibromo-2,5-dimethylbenzene. (0116) Functionalized 1,4-dibromobenzene (8.00 mmol, 1.00 equiv), 1-(2-tetrahydropyranyl)-1H-pyrazole-4-boronic acid pinacol ester (5.56 g, 20.0 mmol, 2.50 equiv), and K3PO4 (8.48 g, 40.0 mmol, 5.00 equiv) were suspended in toluene (16 mL) in a 40-mL glass scintillation vial equipped with a magnetic stir bar, which was then sparged with Ar for 10 min. The vial was uncapped quickly to add XPhos Pd G2 (1.26 g, 1.60 mmol, 0.200 equiv) and then briefly purged with Ar, sealed with a PTFE-lined cap, and heated to 110 C. with stirring for 2 days. After 2 days, the reaction mixture was cooled to room temperature, exposed to air, concentrated under reduced pressure, and diluted with 250 mL of diethyl ether. The ether layer was then washed with saturated aqueous NaHCO3 (5×250 mL), dried over MgSO4, and concentrated under reduced pressure to yield a yellow oil, which was used in the subsequent reaction without additional purification. The crude ligand was then dissolved in 60 mL of methanol in a 250-mL round-bottom flask equipped with a magnetic stir bar. To this flask was added 12 mL of concentrated aqueous HCl, and the reaction mixture was stirred at 50 C. for 2 h, during which time a white precipitate formed. The reaction mixture was then filtered, and the filtrate was suspended in water and neutralized with NaHCO3. The precipitate was isolated in a second filtration, washed with water, and dried under reduced pressure to yield a white or beige powder.
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