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Organoboron
Phenylboronic acid
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[ CAS No. 98-80-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 98-80-6
Chemical Structure| 98-80-6
Structure of 98-80-6 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 98-80-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 98-80-6 ]

Product Details of [ 98-80-6 ]

CAS No. :98-80-6 MDL No. :MFCD00002103
Formula : C6H7BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HXITXNWTGFUOAU-UHFFFAOYSA-N
M.W : 121.93 Pubchem ID :66827
Synonyms :
Phenylboron dihydroxide

Calculated chemistry of [ 98-80-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 36.27
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : -0.63
Log Po/w (MLOGP) : 0.26
Log Po/w (SILICOS-IT) : -0.72
Consensus Log Po/w : -0.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.55
Solubility : 3.47 mg/ml ; 0.0284 mol/l
Class : Very soluble
Log S (Ali) : -1.26
Solubility : 6.67 mg/ml ; 0.0547 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.24
Solubility : 7.0 mg/ml ; 0.0574 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 98-80-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 98-80-6 ]

* 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 [ 98-80-6 ]

[ 98-80-6 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 1585-07-5 ]
  • [ 98-80-6 ]
  • [ 5707-44-8 ]
YieldReaction ConditionsOperation in experiment
91.5% With potassium phosphate tribasic heptahydrate; C40H39ClFeNPPd; In toluene; at 60℃; for 4h; General procedure: Aryl bromide (1 mmol), phenylboronic acid (1.2 mmol), K3PO4*7H2O (1 mmol), and catalyst were dissolved in 6 mL tolueneand stirred at 60 C for 4 h. The mixture was quenched with water and extracted with CH2Cl2. After the removal of the solvent, the residue was purified by column chromatography.
73% With potassium phosphate; C32H28N12Ni(2+)*2F6P(1-); triphenylphosphine; In 1,4-dioxane; at 100℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: In a typical reaction, aryl halide (1.0 mmol), phenylboronic acid(1.2 mmol), base (2 mmol), pph3 (10% mmol) and complex 4(2% mmol) and dioxane (4 ml) were stirred at 100 C for 24 h. Thenthe solvent was removed under vacuum. The pure products wereobtained by column chromatography.
60% With potassium carbonate; In ethanol; at 78℃; for 1.5h; General procedure: The catalyst Cu-Pd-4A-TSI was prepared according to the method described in [22]. The catalyst was treated at 120 C for 1 h before the reaction. Boronic acid (1.5 mmol or 1.2 mmol), aryl halide (1 mmol), potassium carbonate (3 mmol) and the pretreated catalyst Cu-Pd-4A-TSI (0.1 g; 2.26 mol% Pd and 9.86 mol% Cu) were stirred in 5 ml refluxing ethanol for 1 or 1.5 h. Then the solid was filtered out, and washed with ethanol. The filtrate was evaporated. The residue was extracted three times with dichloromethane and with water. The organic phase was dried over anhydrous sodium sulphate, filtered and the solvent was evaporated. The product was subjected to either GC-MS analysis and/or 1H NMR. If required, the product was recrystallized.
With sodium carbonate; In ethanol; water; at 80℃; for 2h;Catalytic behavior; Typically, halobenzene (0.5 mmol), benzene boronic acid (0.6 mmol), base (Na2CO3 or K2CO3) (1 mmol), catalyst (20 mg, 0.59 mol% Pd) and 6 mL of solvent [H2O, EtOH or H2O/EtOH (2:1, v/v)] were introduced into a round bottomed flask under stirring. The reaction was allowed to proceed at the desired reaction temperature for appropriate time. After reaction completion, the catalyst was separated by centrifuging and the obtained products were extracted with diethyl ether. The extracted phase was subjected to GC and GC massfor quantitative detection of products using toluene as the internal standard.

Reference： [1]RSC Advances,2015,vol. 5,p. 49568 - 49576
[2]Tetrahedron Letters,1994,vol. 35,p. 3277 - 3280
[3]Chemistry - A European Journal,2010,vol. 16,p. 8047 - 8053
[4]Chemical Communications,2009,p. 3750 - 3752
[5]Australian Journal of Chemistry,2013,vol. 66,p. 218 - 226
[6]European Journal of Organic Chemistry,2017,vol. 2017,p. 1337 - 1342
[7]Journal of Organometallic Chemistry,2016,vol. 824,p. 124 - 130
[8]Chemical Communications,2011,vol. 47,p. 7686 - 7688
[9]Organometallics,2014,vol. 33,p. 6241 - 6246
[10]Journal of Organometallic Chemistry,2016,vol. 808,p. 12 - 22
[11]Catalysis Letters,2015,vol. 145,p. 834 - 839
[12]Catalysis science and technology,2014,vol. 4,p. 1456 - 1464
[13]Catalysis Letters,2016,vol. 146,p. 499 - 508
  • 2
  • [ 13195-50-1 ]
  • [ 98-80-6 ]
  • [ 18150-93-1 ]
Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 779 - 786
[2]Organometallics,2015,vol. 34,p. 4775 - 4780
  • 3
  • [ 13091-23-1 ]
  • [ 98-80-6 ]
  • [ 132038-21-2 ]
  • [ 31872-62-5 ]
Reference： [1]Heterocycles,1999,vol. 51,p. 721 - 726
  • 4
  • [ 62336-24-7 ]
  • [ 98-80-6 ]
  • [ 13885-09-1 ]
Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 9085 - 9088
  • 5
  • [ 108-86-1 ]
  • [ 67665-47-8 ]
  • [ 196207-58-6 ]
  • [ 98-80-6 ]
  • poly(9,9-dioctylfluorene)-alt-co-(9,9\-spirobifluorene), Mn = 14000, Mw/Mn = 1.5; monomer(s): 2,2\-dibromo-9,9\-spirobifluorene; 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene; phenylboronic acid; bromobenzene [ No CAS ]
Reference： [1]Journal of Materials Chemistry,2002,vol. 12,p. 2893 - 2897
  • 6
  • [ 4016-63-1 ]
  • [ 98-80-6 ]
  • [ 79953-03-0 ]
Reference： [1]Synthetic Communications,2006,vol. 36,p. 3713 - 3721
[2]Journal of Organic Chemistry,2003,vol. 68,p. 6767 - 6774
  • 7
  • [ 95-56-7 ]
  • [ 98-80-6 ]
  • [ 7025-06-1 ]
YieldReaction ConditionsOperation in experiment
47% With copper diacetate; triethylamine; In dichloromethane; at 20℃; for 18h;Molecular sieve; A mixture of 2-bromophenol (0.211 ml, 2 mmol), phenylboronic acid (490 mg, 4 mmol), copper acetate (364 mg, 2 mmol), TEA (1.38 ml, 10 mmol) and 4A molecular sieves in DCM (25 ml) was stirred at r.t. for 18 h. The slurry was filtered through celite and concentrated in vacuo. This was then diluted with EtOAc and NaHCO3 solution, extracted and the organic portions were washed with brine and dried (MgSO4). The crude mixture was purified by flash chromatography (hexane) to yield the desired product as a colourless oil, 232 mg, 47 percent yield. R.f. 0.75 (DCM),LCMS: U = 1.3 min (95 percent MeOH in water), m/z M-H 246.84, 248.86,HPLC: U= 2.88 min (90 percent ACN in water), 98percent,1H NMR (CDCl3, 270 MHz,): delta 6.95-7.04 (4H, m, ArH), 7.11 (IH, td, J=Ll, 8.0 Hz,ArH), 7.22-7.37 (3H, m, ArH), 7.61-7.65 (IH, m, ArH), 13C NMR (CDCl3, 68 MHz): 115.0 (ArC), 118.2, 120.7, 123.5, 125.1, 128.8, 129.9, 133.9(ArCH), 153.8, 156.9 (ArC).
15.1% With pyridine; copper diacetate; In dichloromethane; at 20℃; for 18h;Molecular sieve; 1-Bromo-2-phenoxybenzene 2-Bromophenol (1.22 mL, 11.6 mmol), phenylboronic acid (2.8 g, 23.1 mmol), Cu(OAc)2 (4.2 g, 23.1 mmol) and pyridine (4.66 mL, 57.8 mmol) were dissolved in dichloromethane (100 mL) in a reaction vessel holding 1 g of 4 A M.S. and stirred at room temperature for 18 hours. After the reaction was completed, the reaction mixture was diluted with dichloromethane and filtered through Celite. The filtrate was extracted with 1 N NaOH and brine, and the organic layer was dried with anhydrous MgSO4 and filtered again. The filtrate was concentrated under reduced pressure) to obtain 436 mg of the target compound (1.75 mmol, 15.1percent). 1H NMR (300 MHz, CDCl3) delta 7.63 (dd, J=8.1 Hz, J=1.8 Hz, 1H), 7.36-7.23 (m, 3H), 7.13-7.08 (m, 1H), 7.04-6.94 (m, 4H).
612 mg With copper diacetate; triethylamine; In dichloromethane; at 20℃; for 16h;Molecular sieve; To a solution of 2-bromophenol (1 g, 5.84 mmol), phenylboronic acid (1.42 g, 11.69 mmol) and TEA (2.95 g, 29.2 mmol) in DCM (30 mL) was added Cu(OAc)2 (1.05 g, 5.84 mmol) and 4A molecular sieves (500 mg). The reaction mixture was stirred at room temperature over air with a dry tube attached for 16h. The mixture was filtered and the filtrate was washed by water (50 mL) and brine (30 mL). The organic layer was dried over anhydrous Na2S04, filtered and concentrated with the residue purified by column chromatography to give 612 mg of the desired product.
Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 99
[2]Patent: US2014/228568,2014,A1 .Location in patent: Paragraph 0162-0163
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755
[4]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00386
  • 8
  • [ 2923-96-8 ]
  • [ 98-80-6 ]
  • [ 515878-88-3 ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 439 - 446
  • 9
  • [ 7311-63-9 ]
  • [ 98-80-6 ]
  • [ 19163-24-7 ]
YieldReaction ConditionsOperation in experiment
Preparation 7 Preparation of 5-phenyl-2-thiophenecarboxylic Acid Following the procedure of Preparation 1(a), except substituting phenylboronic acid for 4-carboxybenzeneboronic acid and 5-bromo-2-thiophenecarboxylic acid for 3-bromopyridine, afforded the title compound.
EXAMPLE 53; A sealed tube was charged with phenylboronic acid (0.695g, 5.7 mmol), 2-bromo- thiophene-5-carboxylic acid (Ig, 4.8 mmol), Pd(PPh3)4 (277 mg, 0.05 quiv)), sodium carnonate (1.53g, 3 quiv.) in 20 mL dioxane was heated at 100 0C overnight. The mixture was partitioned between EtOAc and IN NaOH, the aqueous phase was washed with EtOAc, then acidified to pH 3. The precipitate was collected by filtration and dried to obtain the acid. A solution of this acid intermediate (0.886g, 4.3mmol) EPO <DP n="56"/>in 40 mL THF was treated with LiAlH4 (0.326g, 8.6 mmol) at O 0C and stirred for 1.5h. The reaction was quenched by saturated solution of potassium tartrate. The mixture was extracted with EtOAc, and organic phase was washed with brine and dried over Na2SO4. Evaporation of the solvent gave the alcohol. To the solution of this alcohol (0.446g, 2.3mmol) in CH2Cl2 (20 mLO, at O0C, was added pyridiniumchlorochromate (0.99g, 4.6 mmol) in one portion. The mixture was stirred at 23 0C overnight. After evaporation of the solvent, the residue was purified on silica gel chromatography using 5percent EtOAc/Hexane to obtain the aldehyde. To a solution of trimethylphosphonoacetate (0.297 mL, 1.8 mmol) in 15 mL THF, at 0 0C, was added n-butyllithium (l,28mL, 1.6M in hexane, 2.04 mmol) dropwisely. After stirred at O0C for 0.5h, a solution of the above aldehyde intermediate (0.326g, 1.7 mmol) in THF (20 mL) was added to the above solution dropwise, and the resulting solution was stirred for 2h at r.t. After evaporation of the solvent, the residue was purified on silica gel chromatography using 5percent EtOAc/hexane to obtain the enoate. A solution of this enoate intermediate (80 mg, 0.327 mmol) and p- toluenesulfonylhydrazide (0.6 Ig, 3.27 mmol) in methanol (60 mL) was refluxed for 3 days. The compound was purified on silica gel chromatography using 4percent EtOAc as eluting solvent to obtain the methyl ester. Following methods described in the above examples, this intermediate was elaborated into Example 53; 1H NMR (DMSO-d6, 500 MHz) delta 11.14(lH,s), 8.47(lH,d), 7.97(1H, d), 7.59(3H, m), 7.38(2H, t), 7.30 (IH, d), 7.25(1H, t), 7.15(1H, t), 6.9O(1H, d), 3.16(2H, t), 2.80(2H, t); LCMS m/z 352.31 (M++.), 350.40 (M+-I).
Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 16346 - 16347
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4915 - 4918
[3]Patent: US6399656,2002,B1
[4]Patent: WO2006/57922,2006,A2 .Location in patent: Page/Page column 54-55
  • 10
  • [ 26452-81-3 ]
  • [ 98-80-6 ]
  • [ 17759-28-3 ]
Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3977 - 3979
  • 11
  • [ 59786-31-1 ]
  • [ 98-80-6 ]
  • [ 850162-87-7 ]
Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2282 - 2293
  • 12
  • [ 1585-07-5 ]
  • [ 624-31-7 ]
  • [ 98-80-6 ]
  • [ 644-08-6 ]
  • [ 5707-44-8 ]
Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 4020 - 4028
  • 13
  • [ 29976-20-3 ]
  • [ 98-80-6 ]
  • [ 66592-70-9 ]
Reference： [1]Synthesis,2006,p. 2855 - 2864
  • 14
  • [ 29976-20-3 ]
  • [ 98-80-6 ]
  • [ 29396-61-0 ]
  • [ 10131-90-5 ]
  • [ 66592-70-9 ]
Reference： [1]Synthesis,2006,p. 2855 - 2864
  • 15
  • [ 98-80-6 ]
  • Merrifield resin-CH2O(CH2)4S-CH2C6H4-Ph-4 [ No CAS ]
  • [ 13885-09-1 ]
Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 9085 - 9088
  • 16
  • [ 98-80-6 ]
  • [ 19163-24-7 ]
Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1585 - 1599
[2]Heterocycles,2014,vol. 89,p. 453 - 464
[3]European Journal of Medicinal Chemistry,2017,vol. 137,p. 96 - 107
  • 17
  • [ 153034-86-7 ]
  • [ 98-80-6 ]
  • [ 42260-39-9 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate;dichloro[di-tert-butyl(chloro)phosphine]palladium(II) dimer; In methanol; for 3.00833h; Example 1; 4-Aminomethyl-cyclohexanecarboxylic acid [2-phenyl-1-(4-phenyl-pyridin-2-yl)- ethyl] -amide, bistrifluoroacetic acid salt; [00335] lA. 2-Chloro-4-phenylpyridine: A flask was charged with 2-chloro- 4-iodo pyridine (2.5g, 10.4 mmol), phenylboronic acid (1.33 g, 10.96 mmol) , K2C03 (4.54 g, 32.88 mmol), PXPd2 (0.186 g, 0.261 mmol), and methanol (34.8 mL). Argon was blown through flask for 30 sec. The dark brown suspension was stirred for 3 h and then filtered, washing with methanol. The filtrate was concentrated to give 2.15 g as a brown solid. Column chromatography (120g silica gel column; gradient elution; 0-35% ethyl acetate/hexane) afforded lA (1.79 g, 90%) as a yellow solid. iH-NMR (400 MHz, CDCI3) 8: 8.43 (d, J = 5.3 Hz, 1H), 7.61 (dd, J = 8.2, 1.5 Hz, 2H), 7.54 (d, J = 2.2 Hz, 1H), 7.52-7.47 (m, 3H), 7.43 (dd, J = 5.1, 1.5 Hz, 1H). ¹3C-NMR (125 MHz, CDC13) No.: 152.2, 151.5, 149.9, 136.8, 129.6,129.2, 127.0, 122.0,120.4. MS 190.0 (M+H) + and 192.0 (M+2+H)+.
84% With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; for 2h;Inert atmosphere; Reflux; To a mixture of 1 (57.36 g, 0.24 mol) in THF/H2O (400 mL/100 mL) were added phenylboric acid (24.2 g, 0.2 mol) and K2CO3 (82.8 g, 0.6 mol). PdCl2(dppf) (2 g) was then added after being charged with N2 three times. The resulting mixture was refluxed for 2 hrs, cooled, and partitioned between a.q. NH4C1 and EtOAc. The aqueous layer was washed with EtOAc. The combined organic layers were washed with water, brine and dried over Na2 S O4. The solvent was removed in vacuo and the residue was purified by silica gel column (PE:EA=10: 1) to afford 32 g of 2 (yield 84%).
82% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water;Inert atmosphere; Reflux; A mixture of 2-chloro-4-iodopyridine (20.0 g, 82 mmol), phenylboronicacid (10.2 g, 82 mmol), Pd(Ph3P)4 (2.84 g 2.46 mmol), sodium carbonate (26.0 g, 246 mmol), DME (600 mL) andwater (150 mL) was degassed with nitrogen and then refluxed overnight. The reaction was concentrated and the extractedwith ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and then vacuum distilled to give 2-chloro-4-phenylpyridine(2.79 g, 12.7 mmol, 82 % yield).
51% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Inert atmosphere; Reflux; To a 1 L three-necked flask were added 2-chloro-4-iodopyridine (50 g, 208.8 mmol), phenyl boronic acid (28 g, 229.7 mmol), Pd(PPh3)4 (12 g, 10.4 mmol), potassium carbonate (86 g, 626 mmol), toluene (500 mL) and water (200 mL), and then the resulting reaction mixture was heated to reflux for 12 h under N2 protection. Then the reaction solution was cooled to room temperature, separated, the organic phase was collected, the water phase was extracted with EA for several times, and the organic phase was combined, dried with MgSO4 and evaporated to dryness, purified via silica gel column chromatography, eluting with EA:PE=1:50 (v:v), to afford intermediate 1 (20 g, 51% yield) as a white solid.

Reference： [1]Inorganic Chemistry,2017,vol. 56,p. 8244 - 8256
[2]Patent: WO2005/123680,2005,A1 .Location in patent: Page/Page column 76
[3]Patent: WO2010/94242,2010,A1 .Location in patent: Preparation III.1
[4]Patent: EP2730583,2014,A1 .Location in patent: Paragraph 0229; 0230
[5]Patent: US2019/225635,2019,A1 .Location in patent: Paragraph 0132; 0133
  • 18
  • potassium phosphate [ No CAS ]
  • argon [ No CAS ]
  • [ 99-90-1 ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 92-91-1 ]
YieldReaction ConditionsOperation in experiment
176 mg (90%) palladium diacetate; In tetrahydrofuran; nitrogen; toluene; EXAMPLE 45 Synthesis of 4-acetylbiphenyl from an aryl bromoide utilizing 0.000001 mol percent Pd An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with phenylboronic acid (228 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol), and 4-bromoacetophenone (199 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and toluene (1.5 mL) was added through a rubber septum. In a separate flask in a nitrogen filled glovebox, palladium acetate (4.5 mg, 0.02 mmol) and 2-(di-tert-butylphosphino)biphenyl (12.0 mg, 0.04 mmol) were dissolved in 20 ml, THF under argon. A portion of this solution (10 muL, 0.00001 mmol Pd, 0.001 mol percent Pd) was added to a second flask contaninig 10 mL THF). A portion of this second solution (10 muL, 0.00000001 mmol Pd, 0.000001 mol percent Pd) was added to the reaction mixture, followed by additional toluene (1.5 mL) through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was heated to 100° C. with stirring until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 176 mg (90percent) of the title compound.
176 mg (90%) palladium diacetate; In tetrahydrofuran; nitrogen; toluene; Example 45 Synthesis of 4-acetylbiphenyl from an aryl bromoide Utilizing 0.000001 mol percent Pd An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with phenylboronic acid (228 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol), and 4-bromoacetophenone (199 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and toluene (1.5 mL) was added through a rubber septum. In a separate flask in a nitrogen filled glovebox, palladium acetate (4.5 mg, 0.02 mmol) and 2-(di-tert-butylphosphino)biphenyl (12.0 mg, 0.04 mmol) were dissolved in 20 mL THF under argon. A portion of this solution (10 muL, 0.00001 mmol Pd, 0.001 mol percent Pd) was added to a second flask contaninig 10 mL THF). A portion of this second solution (10 muL, 0.00000001 mmol Pd, 0.000001 mol percent Pd) was added to the reaction mixture, followed by additional toluene (1.5 mL) through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was heated to 100° C. with stirring until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 176 mg (90percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 19
  • [ 18982-54-2 ]
  • argon [ No CAS ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 2928-43-0 ]
YieldReaction ConditionsOperation in experiment
153 mg (83%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 35 Synthesis of 2-hydroxymethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 2-bromobenzyl alcohol (187 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 153 mg (83percent) of the title compound.
153 mg (83%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 35 Synthesis of 2-hydroxymethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 2-bromobenzyl alcohol (187 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered througth celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 153 mg (83percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 20
  • potassium phosphate [ No CAS ]
  • [ 99-91-2 ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 92-91-1 ]
YieldReaction ConditionsOperation in experiment
178 mg (91%) palladium diacetate; In tetrahydrofuran; toluene; EXAMPLE 44 Synthesis of 4-acetylbiphenyl from an Aryl Chloride Utilizing 0.02 mol percent Pd An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with phenylboronic acid (228 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol). The tube was evacuated and backfilled with argon, and toluene (1.5 mL) and 4-chloroacetophenone (0.13 mL, 1.0 mmol) were added through a rubber septum. In a separate flask, palladium acetate (2.2 mg, 0.01 mmol) and 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol) were dissolved in 5 mL THF under argon. A portion of this solution (100 muL, 0.0002 mmol Pd, 0.02 mol percent Pd) was added to the reaction mixture, followed by additional toluene (1.5 mL) through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was heated to 100° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 178 mg (91percent) of the title compound.
178 mg (91%) palladium diacetate; In tetrahydrofuran; toluene; Example 44 Synthesis of 4-acetylbiphenyl from an aryl chloride Utilizing 0.02 mol percent Pd An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with phenylboronic acid (228 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol). The tube was evacuated and backfilled with argon, and toluene (1.5 mL) and 4-chloroacetophenone (0.13 mL, 1.0 mmol) were added through a rubber septum. In a separate flask, palladium acetate (2.2 mg, 0.01 mmol) and 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol) were dissolved in 5 mL THF under argon. A portion of this solution (100 muL, 0.0002 mmol Pd, 0.02 mol percent Pd) was added to the reaction mixture, followed by additional toluene (1.5 mL) through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was heated to 100° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 178 mg (91percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 21
  • [ 623-03-0 ]
  • argon [ No CAS ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 2920-38-9 ]
YieldReaction ConditionsOperation in experiment
159 mg (89%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 32 Synthesis of 4-cyanobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-chlorobenzonitrile (136 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 ml), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 159 mg (89percent) of the title compound.
159 mg (89%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 32 Synthesis of 4-cyanobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-chlorobenzonitrile (136 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 159 mg (89percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 22
  • [ 103-88-8 ]
  • argon [ No CAS ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 4075-79-0 ]
YieldReaction ConditionsOperation in experiment
182 mg (86%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 38 Synthesis of N-acetyl-4-aminobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4'-bromoacetanilide (214 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 182 mg (86percent) of the title compound.
182 mg (86%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 38 Synthesis of N-acetyl-4-aminobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4'-bromoacetanilide (214 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 182 mg (86percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 23
  • [ 106-41-2 ]
  • argon [ No CAS ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 92-69-3 ]
YieldReaction ConditionsOperation in experiment
154 mg (91%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 34 Synthesis of 4-hydroxybiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-bromophenol (173 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 154 mg (91percent) of the title compound.
154 mg (91%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 34 Synthesis of 4-hydroxybiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-bromophenol (173 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 154 mg (91percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 24
  • argon [ No CAS ]
  • [ 100-00-5 ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 92-93-3 ]
YieldReaction ConditionsOperation in experiment
196 mg (98%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 39 Synthesis of 4-nitrobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 1-chloro-4-nitrobenzene (158 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was scaled with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 196 mg (98percent) of the title compound.
196 mg (98%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 39 Synthesis of 4-nitrobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 1-chloro-4-nitrobenzene (158 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 196 mg (98percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 25
  • [ 553-94-6 ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 7372-85-2 ]
YieldReaction ConditionsOperation in experiment
149 mg (82%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 36 Synthesis of 2,5-dimethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg. 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-bromo-p-xylene (0.138 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 149 mg (82percent) of the title compound.
149 mg (82%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 36 Synthesis of 2,5-dimethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-bromo-p-xylene (0.138 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 149 mg (82percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 26
  • [ 576-22-7 ]
  • [ 224311-51-7 ]
  • [ 98-80-6 ]
  • [ 3976-34-9 ]
YieldReaction ConditionsOperation in experiment
144 mg (79%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 40 Synthesis of 2,6-dimethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-bromo-m-xylene (0.144 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at 65° C. until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 144 mg (79percent) of the title compound.
144 mg (79%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 40 Synthesis of 2,6-dimethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-bromo-m-xylene (0.144 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at 65° C. until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 144 mg (79percent) of the title compound.
Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1
  • 27
  • [ 5467-57-2 ]
  • [ 98-80-6 ]
  • [ 132-60-5 ]
Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2912 - 2920
  • 28
  • [ 529-84-0 ]
  • [ 98-80-6 ]
  • C16H11BO4 [ No CAS ]
Reference： [1]Molecules,2010,vol. 15,p. 2347 - 2356
  • 29
  • [ 25309-64-2 ]
  • [ 98-80-6 ]
  • [ 5707-44-8 ]
Reference： [1]Chinese Journal of Chemistry,2011,vol. 29,p. 525 - 530
[2]Advanced synthesis and catalysis,2012,vol. 354,p. 2911 - 2915,5
[3]ChemCatChem,2013,vol. 5,p. 142 - 145
[4]Chemical Communications,2010,vol. 46,p. 6524 - 6526
[5]Applied Organometallic Chemistry,2013,vol. 27,p. 519 - 522
  • 30
  • [ 908240-50-6 ]
  • [ 98-80-6 ]
  • [ 1262866-86-3 ]
YieldReaction ConditionsOperation in experiment
67% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 3h; After 2,4-dichloropyrido[3,4-d]pyrimidin (5 g, 24.9 mmol), phenylboronic acid (3.6 g, 29.9 mmol), Pd(PPh3)4 (1/15 g, 0.996 mmol), sodium carbonate aqueous solution (87 mL) , and ethanol (87 mL) were dissolved in toluene (180 mL), the mixture was stirred under reflux at 120 C for 3 hours. When the reaction was completed, an organic layer was extracted with ethyl acetate and remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound B-I (4 g, 16.5 mmol, 67 percent)
Reference： [1]Patent: WO2011/14039,2011,A1 .Location in patent: Page/Page column 20
[2]Organic Letters,2017,vol. 19,p. 6368 - 6371
  • 31
  • [ 908240-50-6 ]
  • [ 98-80-6 ]
  • [ 1262866-87-4 ]
Reference： [1]Patent: WO2011/14039,2011,A1
  • 32
  • [ 78775-11-8 ]
  • [ 98-80-6 ]
  • [ 1256468-34-4 ]
Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 4276 - 4286
  • 33
  • [ 62224-19-5 ]
  • [ 98-80-6 ]
  • [ 19163-24-7 ]
Reference： [1]ChemMedChem,2011,vol. 6,p. 362 - 377
  • 34
  • [ 98-80-6 ]
  • [ 13885-09-1 ]
Reference： [1]European Journal of Organic Chemistry,2012,p. 2127 - 2131
[2]Organic Letters,2013,vol. 15,p. 5302 - 5305
[3]Organic Letters,2013,vol. 15,p. 6186 - 6189
[4]Chemical Communications,2014,vol. 50,p. 4686 - 4689
[5]Organic Letters,2017,vol. 19,p. 1842 - 1845
  • 35
  • [ 25309-64-2 ]
  • [ 98-80-6 ]
  • [ 92-52-4 ]
  • [ 5707-44-8 ]
YieldReaction ConditionsOperation in experiment
10%; 88% With trans-1,2-Diaminocyclohexane; potassium tert-butylate; silver(I) acetate; In dimethyl sulfoxide; at 150℃; for 7.5h;Inert atmosphere; General procedure: To a stirred solution of boronic acid (1.2 mmol) and AgOAc (16 mg, 10 mol percent) in dry DMSO (3 ml) was added aryl iodides/bromides (1 mmol) followed by trans-1,2-diaminocyclohexane (0.006 ml, 10 mol percent) and KOtBu (224 mg, 2 equiv) under a nitrogen atmosphere. The mixture was heated to 150 C and the progress was monitored by TLC. After completion, the reaction mixture was washed with EtOAc-H2O and the organic phase was separated and dried over Na2SO4. The EtOAc was evaporated followed by flash column purification on silica gel to obtain the pure products.#10;
Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 7023 - 7027
  • 36
  • [ 34028-17-6 ]
  • [ 98-80-6 ]
  • [ 2622-63-1 ]
Reference： [1]Organic Letters,2012,vol. 14,p. 5980 - 5983
  • 37
  • [ 3621-82-7 ]
  • [ 98-80-6 ]
  • [ 15952-20-2 ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 6h;Inert atmosphere; General procedure: A 1,4-dioxane solution (3 mL) of 1, arylboronic acid (1.2 equiv), aqueous K2CO3 (2.0 M, 1.0 mL) and Pd(PPh3)4 (3 mol percent) was heated at 80 °C for 6 h under argon atmosphere. After cooling to 20 °C, H2O was added and the reaction mixture was extracted with CH2Cl2 (3×25 mL). The organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, heptane/EtOAc).#10;
Reference： [1]Tetrahedron,2013,vol. 69,p. 2081 - 2086
  • 38
  • [ 1480-65-5 ]
  • [ 98-80-6 ]
  • 2-fluoro-5-phenyl-pyridine [ No CAS ]
Reference： [1]Organic Letters,2013,vol. 15,p. 2716 - 2719
  • 39
  • [ 26452-80-2 ]
  • [ 98-80-6 ]
  • [ 57311-18-9 ]
  • [ 42260-39-9 ]
Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 7758 - 7763
  • 40
  • [ 26452-80-2 ]
  • [ 98-80-6 ]
  • [ 57311-18-9 ]
  • [ 26274-35-1 ]
  • [ 42260-39-9 ]
Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 7758 - 7763
  • 41
  • [ 98-80-6 ]
  • [ 224311-51-7 ]
Reference： [1]Chemical Communications,2014,vol. 50,p. 2193 - 2195
  • 42
  • [ 1632-83-3 ]
  • [ 98-80-6 ]
  • [ 2622-63-1 ]
YieldReaction ConditionsOperation in experiment
75% With iron(III) chloride; copper(II) acetate dihydrate; palladium dichloride; In N,N-dimethyl-formamide; at 120℃; for 24h; General procedure: Azole (0.5 mmol), arylboronic acid (1.0 mmol), PdCl2(0.05 mmol), Cu(OAc)2·H2O (0.25 mmol), FeCl3 (0.25mmol) and DMF (2.0 mL) were taken in a 25 mL two-neckflask. The mixture was heated at 120 °C in air for 24 h bymagnetic stirring. After cooling to room temperature, theproduct was diluted with H2O (5 mL) and extracted withEtOAc (415 mL). The extracts were combined and washedby brine (310 mL), dried over MgSO4, filtered, and evaporated,and purified by chromatography on silica gel to obtainthe desired products with ethyl acetate/hexane(v/v=1:11:10). The products were characterized by theirspectral and analytical data and compared with those of theknown compounds.
Reference： [1]Letters in Organic Chemistry,2013,vol. 10,p. 668 - 673
  • 43
  • [ 129488-10-4 ]
  • [ 98-80-6 ]
  • tert-butyl 5-anilino-1H-indazole-1-carboxylate [ No CAS ]
Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 7539 - 7543
  • 44
  • [ 38573-88-5 ]
  • [ 98-80-6 ]
  • [ 67277-32-1 ]
Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 551 - 555
[2]Applied Organometallic Chemistry,2015,vol. 29,p. 87 - 89
  • 45
  • [ 39745-40-9 ]
  • [ 98-80-6 ]
  • [ 1214387-73-1 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 18h; A deoxygenated mixture of 2-chloi -6-methylpyridin-3-amine (200 mg, 1.56 mmol), phenylboronic acid (381 mg, 3.13 mmol), Pd(dppf Cl2 (5 mg, 0.007 mmol), and K2CO3 (646 mg, 4.68 mmol) in a 10: 1 mixture of 1 ,4-dioxane: water (33 mL) was heated at 80 °C for 18 h. The mixture was cooled and the organic layer was separated and washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was further purified by TLC (PE: EtOAc = 2: 1 ) to give the title compound as a white solid. MS: m/z = 171 (M+H).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 18h; Example of reaction scheme VII: Intermediate 46-Methyl-2-phenylpyridin-3-amineA deoxygenated mixture of 2-chloro-6-methylpyridin-3 -amine (200 mg, 1.56 mmol), phenylboronic acid (381 mg, 3.13 mmol), Pd(dppf)2Cl2(5 mg, 0.007 mmol), and K2C03(646 mg, 4.68 mmol) in a 10: 1 mixture of 1,4-dioxane: water (33 mL) was heated at 80 °C for 18 h. The mixture was cooled and the organic layer was separated and washed with brine, dried over anhydrous Na2S04and concentrated. The residue was further purified by TLC (PE: EtOAc = 2: 1) to give the title compound as a white solid. MS: m/z = 111 (M+H).
Reference： [1]Patent: WO2015/42085,2015,A2 .Location in patent: Page/Page column 32
[2]Patent: WO2015/39333,2015,A1 .Location in patent: Page/Page column 33
  • 46
  • [ 83647-43-2 ]
  • [ 98-80-6 ]
  • [ 76350-90-8 ]
YieldReaction ConditionsOperation in experiment
74.62% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 12h;Inert atmosphere; To a solution of 20.00 g (99.47 mmol, 1.0 eq) of (3-bromo-2-methyl-phenyl)methanol 1A and 24.26 g (198.94 mmol, 2.0 eq) of phenylboronic acid in 156 mL of toluene and 52mL of EtOH, were added 812.3 mg (0.995 mmol, 0.01 eq) of Pd(dppf)Cl2.CH2Cl2 and 25.07g (2 M, 149.21 mL, 3.0 eq) of NaHCC under nitrogen gas. The mixture was stirred at 80C for 12 hours. The mixture was separated, and the aqueous phase was extracted with 2 x 400 mL of ethyl acetate (EtOAc). The combined organic phase was washed with 2 x 200 mL of brine, dried over Na2SC>4, filtered and the solvent was concentrated. The residue was purified by column eluted with petroleum ether/ethyl acetate = 25/1-10/1 to give crude product (25 g) as a yellow solid. The solid was smashed in 100 mL of petroleum ether, and the suspension was filtered to give 15.00 g (74.62%) of (2-methyl-[l,l'-biphenyl]-3-yl)methanol as a white solid. lH NMR (400 MHz, CDC13): delta 7.40-7.31 (m, 4H) 7.25-7.22 (m, 3H) 4.75-4.74 (m, 2H) 2.21 (m, 3H) 1.62~1.59(m, 1H).
73% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; water; toluene; at 80℃; for 12h;Inert atmosphere; Sealed tube; To a stirred solution of (3-bromo-2-methylphenyl)methanol (4, 1 g, 5 mmol), phenyl boronic acid (5, 1.4 g, 10 mmol) in toulene (12 mL) and EtOH (4 mL) were added PdCl2(dppf).DCM (0.04 g, 0.05 mmol) and 2M aqueous NaHC03 solution (4 mL), the reaction mixture was degasified with nitrogen gas for 10 min. The reaction mixture was then heated in a seal tube at 80 C for 12 h. The reaction mixture was filtered through celite; the filtrate was diluted with water and extracted with ethyl acetate (2 x 100 mL). The organic layer was then dried over sodium sulfate, evaporated and the crude was purified on combiflash MPLC using 20% ethyl acetate in hexanes as eluent to afford (2-methyl-[l, l'-biphenyl]-3-yl)methanol as off-white solid (6, Yield: 0.81 g, 73%). LCMS (ES) m/z = 199.1 [M+H]+
68.9% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 3h;Inert atmosphere; The compound I-1C (2 g, 10 mmol) obtained in the previous step was dissolved in dioxane (30 ml).Add 2N aqueous potassium carbonate solution (10 ml),Then, phenylboric acid (1.46 g, 12 mmol) and tetrakistriphenylphosphine palladium (150 mg, 0.12 mmol) were added, and the obtained reaction solution was replaced with nitrogen three times.The reaction was carried out at 100 C for 3 hours under a nitrogen atmosphere, and TLC showed the reaction was completed.After the methanol was rotated under reduced pressure, a saturated ammonium chloride solution (250 ml) was added.The mixture was extracted with ethyl acetate (150 mL×3), and then evaporated. Ethyl acetate = 10/1 (volume ratio V / V)),Compound I-1D (1.36 g, pale yellow solid) was obtained.Yield: 68.9%.
2 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 0.5h;Inert atmosphere; A mixture of (3-bromo-2-methylphenyl)methanol (2.071 g, 10.3 mmol), phenylboronic acid (2.51 g, 20.60 mmol) and [l,l'-bis(diphenylphosphino)ferrocene] dichloropalladium (II) dichloromethane complex (0.084 g, 0.103 mmol) in toluene (15.45 ml) and ethanol (5.15 ml) was placed under argon. To this solution was added sodium bicarbonate, 2M (15.45 ml, 30.9 mmol) and the mixture was heated at 80 C for 30 min. The reaction mixture was diluted with 20 mL ethyl acetate and 5 mL water. The organic portion was concentrated by rotatory evaporation. The crude product was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford 2 g of an off-white solid. 1H NMR (400MHz, CHLOROFORM-d) delta 7.47-7.29 (m, 7H), 7.23 (s, 1H), 4.80 (d, J=5.6 Hz, 2H), 2.27 (s, 3H), 1.63-1.59 (m, 1H).
2 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 0.5h;Inert atmosphere; A mixture of (3-bromo-2-methylphenyl)methanol (2.071 g, 10.3 mmol), phenylboronic acid (2.51 g, 20.60 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane complex (0.084 g, 0.103 mmol) in toluene (15.45 mL) and ethanol (5.15 mL) was placed under argon. To this solution was added sodium bicarbonate, 2M (15.45 mL, 30.9 mmol) and the mixture was heated at 80 C. for 30 minutes. The reaction mixture was diluted with 20 mL ethyl acetate and 5 mL water. The organic portion was concentrated by rotatory evaporation. The crude product was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford 2 g of an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta 7.47-7.29 (m, 7H), 7.23 (s, 1H), 4.80 (d, J=5.6 Hz, 2H), 2.27 (s, 3H), 1.63-1.59 (m, 1H).
4.58 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 0.5h;Inert atmosphere; A mixture of compound 2 (4.6 g, 22.8 mmol), phenylboronic acid 3 (5.65 g, 46.3 mmol) and [ 1 , 1 ' -bis (diphenylphosphino) - ferrocene ] dichloropalladium ( I I ) dichloromethane complex (0.188 g, 0.103 mmol) in toluene (34.5 mL) and ethanol (11.3 mL) was placed under argon. To this solution sodium bicarbonate, 2M (34.5 mL, 69.0 mmol) was added and the mixture was heated at 80 C for 30 min. Ethyl acetate (44 mL) and (11 mL) water were added to the reaction mixture. The organic extract was concentrated by rotatory evaporation. The crude product was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford 4.58 g of an off-white solid, mp: 58.0- 59.5 C; 1H NMR (600 MHz, CDC13) delta [ppm] : 7.43-7.40 (m, 3H) , 7.35 (m, 1H) , 7.31-7.29 (m, 2H) , 1H) , 7.26 (t, J=7.6 Hz, 1H) , 7.20 (dd, Jl=7.6 Hz, J2=1.3 Hz, 1H) , 4.78 (s, 2H) , 2.25 (s, 3H) ; 13C NMR (151MHz, DMSO-d6) delta [ppm]: 143.0, 142.2, 140.0, 133.8, 129.7, 129.5, 128.2, 127.0, 126.9, 125.7, 64.2, 16.0; IR V (ATR cm-1) : 3365, 3054, 1601, 1469, 1047, 757.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5857 - 5867
[2]Patent: WO2018/200571,2018,A1 .Location in patent: Page/Page column 44-45
[3]Patent: WO2019/87214,2019,A1 .Location in patent: Paragraph 000121
[4]Patent: CN110092740,2019,A .Location in patent: Paragraph 0115; 0120-0121; 0128-0130
[5]Patent: WO2015/34820,2015,A1 .Location in patent: Page/Page column 42
[6]Patent: US2015/291549,2015,A1 .Location in patent: Paragraph 0210; 0211
[7]Patent: WO2017/118762,2017,A1 .Location in patent: Page/Page column 39; 40
  • 47
  • [ 89891-69-0 ]
  • [ 98-80-6 ]
  • 5-cyano-[1,1'-biphenyl]-2-carbaldehyde [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 2893 - 2899
  • 48
  • [ 89891-69-0 ]
  • [ 98-80-6 ]
  • 2,5-bis(5-cyano-[1,1′-biphenyl]-2-yl)-1,4-bis(4-octylphenyl)-1,4-dihydropyrrolo[3,2-b]pyrrole [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 2893 - 2899
  • 49
  • [ 1120-95-2 ]
  • [ 98-80-6 ]
  • [ 15150-84-2 ]
Reference： [1]Organic Letters,2015,vol. 17,p. 5878 - 5881
  • 50
  • [ 68176-57-8 ]
  • [ 98-80-6 ]
  • C16H19BN2 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 969 - 980
[2]Journal of Organic Chemistry,2016,vol. 81,p. 969 - 980
  • 51
  • C16H19BN2 [ No CAS ]
  • [ 68176-57-8 ]
  • [ 98-80-6 ]
Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 969 - 980
  • 52
  • 2-chloropyridin-4-yl fluorosulfate [ No CAS ]
  • [ 98-80-6 ]
  • [ 42260-39-9 ]
Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 5692 - 5697
  • 53
  • sodium p-ethylbenzenesulfinic acid [ No CAS ]
  • [ 98-80-6 ]
  • [ 5707-44-8 ]
Reference： [1]RSC Advances,2014,vol. 4,p. 57923 - 57928
  • 54
  • [ 73583-37-6 ]
  • [ 98-80-6 ]
  • [ 42260-39-9 ]
Reference： [1]Patent: WO2016/42775,2016,A1 .Location in patent: Paragraph 0258; 0260
  • 55
  • [ 144649-99-0 ]
  • [ 98-80-6 ]
  • [ 1245529-62-7 ]
YieldReaction ConditionsOperation in experiment
80% With C25H16O6*C4H11N*H2O; palladium diacetate; potassium carbonate; In water; at 80℃; for 1 - 2h; General procedure: A mixture of aryl halide (1.0 mmol), phenylboronic acid (1.2 mmol), K2CO3 (2.0 mmol), novel ligand (0.1 mol percent, 0.5 mg), and Pd(OAc)2 (0.1 molpercent, 0.23 mg) was heated in water (5 ml) at 80 °C temperature. The progress of the reaction is monitor by TLC. After the completion of the reaction, ethyl acetate (10 ml) was added to the reaction mixture and extracted with ethyl acetate (3 x 10 ml). The combined organic layer was dried with anhyd. Na2SO4 and the solvent were concentrated in vacuum to obtain a light yellow-white solid. The residue was purified by silica gel column chromatography (5-10percent EtOAc in hexane) to afford the corresponding pure products.
80% With 2-hydroxy-3-(p-tolyl)-2,3-dihydroindan-1-one; palladium diacetate; potassium carbonate; In ethanol; at 20℃; General procedure: A mixture of aryl halide/tosylate (1.0 mmol), phenylboronic acid (1.2 mmol), K2CO3 (2.0 mmol), ligand (0.1 molpercent) and Pd(OAc)2 (0.1 molpercent) in EtOH (5 mL) was stirred at r.t. The progress of the reaction was monitored by TLC. Upon completion of the reaction, solvent was removed under reduced pressure. Water (10 mL) was added to the reaction mixture and extracted with EtOAc (3 × 10 mL). The combined organic layer was dried with anhydrous Na2SO4 and the solvent was concentrated in vacuum to obtain a light yellow-white solid. The residue was purified by silica gel column chromatography (EtOAc?hexane,5?10percent) to afford the corresponding pure products.
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3785 - 3789
[2]Synthesis,2017,vol. 49,p. 4372 - 4382
  • 56
  • [ 924-44-7 ]
  • [ 6292-59-7 ]
  • [ 98-80-6 ]
  • (S)-ethyl 2-(4-(tert-butyl)phenylsulfonamido)-2-phenylacetate [ No CAS ]
Reference： [1]Organic Letters,2016,vol. 18,p. 4116 - 4119
  • 57
  • [ 924-44-7 ]
  • [ 6292-59-7 ]
  • [ 98-80-6 ]
  • ethyl 2-(4-(tert-butyl)phenylsulfonamido)-2-phenylacetate [ No CAS ]
Reference： [1]Organic Letters,2016,vol. 18,p. 4116 - 4119
  • 58
  • [ 28342-75-8 ]
  • [ 98-80-6 ]
  • 4',6'-difluoro-1,1': 3',1''-terphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 g With potassium phosphate; In water; isopropyl alcohol; toluene; for 1h;Inert atmosphere; Reflux; Under a nitrogen atmosphere and at reflux temperature there was added 1,5-bromo-2,4-difluorobenzene (90.0 g), phenylboronic acid (which 88.6 g of), tripotassiumphosphate (154.0g), Pd-132 (Johnson Matthey (JohnsonMatthey)) (1.6g), toluene (900ml),isopropanol (300ml) and water (150ml) of the flask was heated for 1 hour. After stoppingthe reaction, the reaction solution was cooled until room temperature and water wasadded to carry out liquid separation. After the solvent was distilled off under reducedpressure, silica gel short column (eluent: heptane / toluene = 1/2 (volume ratio)) to bepurified, thereby obtaining 4 ', 6'-difluoro-1,1': 3 ', 1' - terphenyl (86.0g).
Reference： [1]Patent: CN105431439,2016,A .Location in patent: Paragraph 0989; 0990; 0991
  • 59
  • [ 106-53-6 ]
  • [ 54198-88-8 ]
  • [ 98-80-6 ]
  • C17H14N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% General procedure: A one dram vial equipped with a stir bar was charged with <strong>[54198-88-8]2-(chloromethyl)pyrimidine</strong> (12.mg,0.070 mmol), 4-bromothiophenol (13.06 mg, 0.070 mmol), and cesium carbonate (95.37 mg, 0.290 mmol). The solids were then dissolved in 1,4-Dioxane (0.327 mL) and stirred at 90 °C for 20 min before the vial was removed from the heat. At this time pyridine-3-boronic acid (11.62 mg, 0.090 mmol), water (36 lL), and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (5.34 mg, 0.010 mmol) were added to the reaction mixture followed by a thirty second purge with argon. The reaction vessel was allowed to stir at 90 °C for anadditional two hours. After being allowed to cool to room temperature the crude reaction mixture was filtered over a thin celite plug in a phase separator with EtOAc (10 mL) and the resulting organics concentrated before crude product was purified using Gilson reverse phase automated system (30 50 mm column, 5?50percent MeCN in 0.1percent Aq. TFA, 5 min gradient). Fractions containing product by LC/MS were pooled and quenched with sat. sodium bicarbonate before being extracted with DCM (5 mL) and dried to afford 2-[[4-(3-pyridyl)phenyl]sulfanylmethyl]pyrimidine (12d,17.6 mg,0.063 mmol, 87percent) as a yellow solid.
Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 112 - 116
  • 60
  • [ 54198-88-8 ]
  • [ 98-80-6 ]
  • 2-halobenzene-1-thiol [ No CAS ]
  • C17H14N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% General procedure: A one dram vial equipped with a stir bar was charged with <strong>[54198-88-8]2-(chloromethyl)pyrimidine</strong> (12.mg,0.070 mmol), 4-bromothiophenol (13.06 mg, 0.070 mmol), and cesium carbonate (95.37 mg, 0.290 mmol). The solids were then dissolved in 1,4-Dioxane (0.327 mL) and stirred at 90 °C for 20 min before the vial was removed from the heat. At this time pyridine-3-boronic acid (11.62 mg, 0.090 mmol), water (36 lL), and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (5.34 mg, 0.010 mmol) were added to the reaction mixture followed by a thirty second purge with argon. The reaction vessel was allowed to stir at 90 °C for anadditional two hours. After being allowed to cool to room temperature the crude reaction mixture was filtered over a thin celite plug in a phase separator with EtOAc (10 mL) and the resulting organics concentrated before crude product was purified using Gilson reverse phase automated system (30 50 mm column, 5?50percent MeCN in 0.1percent Aq. TFA, 5 min gradient). Fractions containing product by LC/MS were pooled and quenched with sat. sodium bicarbonate before being extracted with DCM (5 mL) and dried to afford 2-[[4-(3-pyridyl)phenyl]sulfanylmethyl]pyrimidine (12d,17.6 mg,0.063 mmol, 87percent) as a yellow solid.
Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 112 - 116
  • 61
  • [ 54198-88-8 ]
  • [ 98-80-6 ]
  • 3-halobenzene-1-thiol [ No CAS ]
  • C17H14N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% General procedure: A one dram vial equipped with a stir bar was charged with <strong>[54198-88-8]2-(chloromethyl)pyrimidine</strong> (12.mg,0.070 mmol), 4-bromothiophenol (13.06 mg, 0.070 mmol), and cesium carbonate (95.37 mg, 0.290 mmol). The solids were then dissolved in 1,4-Dioxane (0.327 mL) and stirred at 90 °C for 20 min before the vial was removed from the heat. At this time pyridine-3-boronic acid (11.62 mg, 0.090 mmol), water (36 lL), and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (5.34 mg, 0.010 mmol) were added to the reaction mixture followed by a thirty second purge with argon. The reaction vessel was allowed to stir at 90 °C for anadditional two hours. After being allowed to cool to room temperature the crude reaction mixture was filtered over a thin celite plug in a phase separator with EtOAc (10 mL) and the resulting organics concentrated before crude product was purified using Gilson reverse phase automated system (30 50 mm column, 5?50percent MeCN in 0.1percent Aq. TFA, 5 min gradient). Fractions containing product by LC/MS were pooled and quenched with sat. sodium bicarbonate before being extracted with DCM (5 mL) and dried to afford 2-[[4-(3-pyridyl)phenyl]sulfanylmethyl]pyrimidine (12d,17.6 mg,0.063 mmol, 87percent) as a yellow solid.
Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 112 - 116
  • 62
  • [ 54198-88-8 ]
  • [ 98-80-6 ]
  • 4-haloaniline [ No CAS ]
  • C17H15N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% General procedure: A one dram vial equipped with a stir bar was charged with <strong>[54198-88-8]2-(chloromethyl)pyrimidine</strong> (12.mg,0.070 mmol), 4-bromothiophenol (13.06 mg, 0.070 mmol), and cesium carbonate (95.37 mg, 0.290 mmol). The solids were then dissolved in 1,4-Dioxane (0.327 mL) and stirred at 90 °C for 20 min before the vial was removed from the heat. At this time pyridine-3-boronic acid (11.62 mg, 0.090 mmol), water (36 lL), and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (5.34 mg, 0.010 mmol) were added to the reaction mixture followed by a thirty second purge with argon. The reaction vessel was allowed to stir at 90 °C for anadditional two hours. After being allowed to cool to room temperature the crude reaction mixture was filtered over a thin celite plug in a phase separator with EtOAc (10 mL) and the resulting organics concentrated before crude product was purified using Gilson reverse phase automated system (30 50 mm column, 5?50percent MeCN in 0.1percent Aq. TFA, 5 min gradient). Fractions containing product by LC/MS were pooled and quenched with sat. sodium bicarbonate before being extracted with DCM (5 mL) and dried to afford 2-[[4-(3-pyridyl)phenyl]sulfanylmethyl]pyrimidine (12d,17.6 mg,0.063 mmol, 87percent) as a yellow solid.
Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 112 - 116
  • 63
  • [ 54198-88-8 ]
  • [ 98-80-6 ]
  • 4-halophenol [ No CAS ]
  • C17H14N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% General procedure: A one dram vial equipped with a stir bar was charged with <strong>[54198-88-8]2-(chloromethyl)pyrimidine</strong> (12.mg,0.070 mmol), 4-bromothiophenol (13.06 mg, 0.070 mmol), and cesium carbonate (95.37 mg, 0.290 mmol). The solids were then dissolved in 1,4-Dioxane (0.327 mL) and stirred at 90 °C for 20 min before the vial was removed from the heat. At this time pyridine-3-boronic acid (11.62 mg, 0.090 mmol), water (36 lL), and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (5.34 mg, 0.010 mmol) were added to the reaction mixture followed by a thirty second purge with argon. The reaction vessel was allowed to stir at 90 °C for anadditional two hours. After being allowed to cool to room temperature the crude reaction mixture was filtered over a thin celite plug in a phase separator with EtOAc (10 mL) and the resulting organics concentrated before crude product was purified using Gilson reverse phase automated system (30 50 mm column, 5?50percent MeCN in 0.1percent Aq. TFA, 5 min gradient). Fractions containing product by LC/MS were pooled and quenched with sat. sodium bicarbonate before being extracted with DCM (5 mL) and dried to afford 2-[[4-(3-pyridyl)phenyl]sulfanylmethyl]pyrimidine (12d,17.6 mg,0.063 mmol, 87percent) as a yellow solid.
Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 112 - 116
  • 64
  • [ 54198-88-8 ]
  • [ 98-80-6 ]
  • 5-halopyridine-2-thiol [ No CAS ]
  • C16H13N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% General procedure: A one dram vial equipped with a stir bar was charged with <strong>[54198-88-8]2-(chloromethyl)pyrimidine</strong> (12.mg,0.070 mmol), 4-bromothiophenol (13.06 mg, 0.070 mmol), and cesium carbonate (95.37 mg, 0.290 mmol). The solids were then dissolved in 1,4-Dioxane (0.327 mL) and stirred at 90 °C for 20 min before the vial was removed from the heat. At this time pyridine-3-boronic acid (11.62 mg, 0.090 mmol), water (36 lL), and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (5.34 mg, 0.010 mmol) were added to the reaction mixture followed by a thirty second purge with argon. The reaction vessel was allowed to stir at 90 °C for anadditional two hours. After being allowed to cool to room temperature the crude reaction mixture was filtered over a thin celite plug in a phase separator with EtOAc (10 mL) and the resulting organics concentrated before crude product was purified using Gilson reverse phase automated system (30 50 mm column, 5?50percent MeCN in 0.1percent Aq. TFA, 5 min gradient). Fractions containing product by LC/MS were pooled and quenched with sat. sodium bicarbonate before being extracted with DCM (5 mL) and dried to afford 2-[[4-(3-pyridyl)phenyl]sulfanylmethyl]pyrimidine (12d,17.6 mg,0.063 mmol, 87percent) as a yellow solid.
Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 112 - 116
  • 65
  • [ 54198-88-8 ]
  • [ 98-80-6 ]
  • 4-halo-2-fluorophenol [ No CAS ]
  • C17H13FN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% General procedure: A one dram vial equipped with a stir bar was charged with <strong>[54198-88-8]2-(chloromethyl)pyrimidine</strong> (12.mg,0.070 mmol), 4-bromothiophenol (13.06 mg, 0.070 mmol), and cesium carbonate (95.37 mg, 0.290 mmol). The solids were then dissolved in 1,4-Dioxane (0.327 mL) and stirred at 90 °C for 20 min before the vial was removed from the heat. At this time pyridine-3-boronic acid (11.62 mg, 0.090 mmol), water (36 lL), and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (5.34 mg, 0.010 mmol) were added to the reaction mixture followed by a thirty second purge with argon. The reaction vessel was allowed to stir at 90 °C for anadditional two hours. After being allowed to cool to room temperature the crude reaction mixture was filtered over a thin celite plug in a phase separator with EtOAc (10 mL) and the resulting organics concentrated before crude product was purified using Gilson reverse phase automated system (30 50 mm column, 5?50percent MeCN in 0.1percent Aq. TFA, 5 min gradient). Fractions containing product by LC/MS were pooled and quenched with sat. sodium bicarbonate before being extracted with DCM (5 mL) and dried to afford 2-[[4-(3-pyridyl)phenyl]sulfanylmethyl]pyrimidine (12d,17.6 mg,0.063 mmol, 87percent) as a yellow solid.
Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 112 - 116
  • 66
  • [ 100-41-4 ]
  • [ 98-80-6 ]
  • [ 5707-44-8 ]
Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 1786 - 1789
  • 67
  • [ 62473-92-1 ]
  • [ 98-80-6 ]
  • 1,1-dioxo-6-phenyl-1,2-benzothiazol-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.166667h;Microwave irradiation; Step A : 1 , 1 -dioxo-6-phen l-1 ,2-benzothiazol-3-one PdCI2(dppf) (77.90 mg; 0.10 mmol; 0.05 eq.) and phenylboric acid (279.14 mg; 2.29 mmol; 1.20 eq.) were added to a solution of 6-bromo-1 ,1-dioxo-1 ,2-benzothiazol-3-one (500.00 mg; 1.91 mmol; 1.00 eq.) in ethylene glycol dimethyl ether (5.00 ml). A solution of K2C03 (395.50 mg; 2.86 mmol; 1.50 eq.) in water (1.67 ml) was added and the reaction was stirred 10 minutes at 120°C under microwave irradiation. The mixture was then filtered over Whatmann and the filtrate concentrated under reduced pressure. Water was added to the residue and the resulting aqueous phase was washed twice with EtOAc. Then, the aqueous phase was acidified with HCI 1 N and extracted twice with EtOAc. Organic layers were combined, dried over MgS04, filtered and concentrated under reduced pressure to give 1 ,1-dioxo-6-phenyl-1 ,2-benzothiazol-3-one (409.0 mg ; 83 percent) as an orange powder. H NMR (DMSO-d6, 300MHz): delta 8.25 (m, 2H) ; 8.19 (m, 1 H) ; 7.83 (m, 2H) ; 7.52 (m, 3H).
Reference： [1]Patent: WO2017/64277,2017,A1 .Location in patent: Page/Page column 53-54
  • 68
  • [ 20265-35-4 ]
  • [ 98-80-6 ]
  • [ 53698-45-6 ]
Reference： [1]Chemical Communications,2019,vol. 55,p. 9287 - 9290
[2]Journal of the American Chemical Society,2017,vol. 139,p. 9423 - 9426
  • 69
  • [ 74137-36-3 ]
  • [ 98-80-6 ]
  • 2-ethylhexyl 3-((5-methoxy-[1,1'-biphenyl]-3-yl)thio)propanoate [ No CAS ]
Reference： [1]Patent: WO2017/141049,2017,A1
  • 70
  • [ 74137-36-3 ]
  • [ 98-80-6 ]
  • 3-bromo-5-methoxy-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 16h;Inert atmosphere; General procedure: 3-Bromo-5-methoxy-1 ,1 '-biphenyl was synthesised according to general procedures GP13 - from 1 ,3- dibromo-5-methoxybenzene (6.50 g, 24.4 mmol), phenylboronic acid (2.08 g, 17.0 mmol), Pd(PPh3)4 (1 .40 g, 5 molpercent), Na2C03 (6.47 g, 61 .0 mmol), toluene (70 ml_), ethanol (7.0 mL) and water (7.0 ml_); 100 °C, 16 h. Chromatographic purification (hexane) afforded a colourless oil (4.1 g, contained a small amount of impurity), which is used in the subsequent transformation as an impure mixture. H NMR of a pure chromatography fraction (400 MHz, DMSO-c/6) delta: 7.55-7.53 (m, 2H), 7.43-7.42 (m, 2H), 7.37 (d, J = 7.3 Hz, 1 H), 7.32-7.31 (m, 1 H), 7.03 (d, J = 1 .4 Hz, 2H), 3.85 (s, 3H). General procedures GP13 [00693] A mixture of bromide GP13_1 , Pd(PPh3)4, ArB(OR')2, Na2C03, H20, EtOH and toluene was degassed with argon and then stirred at 100 °C for 16 h. After cooling to rt, the mixture was diluted with Et20 and filtered through celite. The organic solution was washed with H20, dried over Na2S04, filtered and the solvent was removed under reduced pressure. The crude was purified by chromatography to afford biaryl GP13_2.
Reference： [1]Patent: WO2017/141049,2017,A1 .Location in patent: Paragraph 00692; 00693; 00884
  • 71
  • [ 98-80-6 ]
  • [ 1022-13-5 ]
Reference： [1]Chemical Science,2017,vol. 8,p. 3852 - 3857
  • 72
  • [ 908240-50-6 ]
  • [ 98-80-6 ]
  • 2-chloro-4-phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine [ No CAS ]
Reference： [1]Organic Letters,2017,vol. 19,p. 6368 - 6371
  • 73
  • [ 363-52-0 ]
  • [ 98-80-6 ]
  • C12H8BFO2 [ No CAS ]
Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 2815 - 2823
  • 74
  • [ 24065-33-6 ]
  • [ 98-80-6 ]
  • [ 19163-24-7 ]
Reference： [1]Organometallics,2017,vol. 36,p. 4191 - 4201
  • 75
  • [ 1585-07-5 ]
  • [ 98-80-6 ]
  • [ 100-41-4 ]
  • [ 5707-44-8 ]
YieldReaction ConditionsOperation in experiment
11%; 26% With (2,4-dibenzyl-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)(dibromo)(pyridine)palladium; tetrabutylammomium bromide; In N,N-dimethyl-formamide; isopropyl alcohol; at 80℃; for 2h;Inert atmosphere; General procedure: The corresponding base (0.7 mmol) (see Tables 2 and 3) was mixed with a solution of aryl halide 3a-l (0.25 mmol), phenylboronic acid (42 mg, 0.35 mmol), and tetrabutylammonium bromide (81 mg, 0.25 mmol) in propan-2-ol (1 mL) in a 7 mL glass vial with a screw cap equipped with a magnetic stirrer. A solution (10 muL) of the corresponding catalyst in DMF was added, and the mixture was purged with argon and stirred at 80 °C for 2-5 h (see Tables 2 and 3). Then the reaction mixture was cooled, and naphthalene (16 mg, 0.125 mmol) as an internal GCMS standard was added. An aliquot (1 muL) of the reaction mixture was dissolved in acetonitrile (1 mL), and the sample was analyzed by GCMS.
Reference： [1]Russian Chemical Bulletin,2018,vol. 67,p. 79 - 84
    Izv. Akad. Nauk, Ser. Khim.,2018,p. 79 - 84,6
  • 76
  • [ 622-98-0 ]
  • [ 98-80-6 ]
  • [ 5707-44-8 ]
YieldReaction ConditionsOperation in experiment
85% With potassium phosphate; C32H28N12Ni(2+)*2F6P(1-); triphenylphosphine; In 1,4-dioxane; at 100℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: In a typical reaction, aryl halide (1.0 mmol), phenylboronic acid(1.2 mmol), base (2 mmol), pph3 (10% mmol) and complex 4(2% mmol) and dioxane (4 ml) were stirred at 100 C for 24 h. Thenthe solvent was removed under vacuum. The pure products wereobtained by column chromatography.
Reference： [1]Journal of Organometallic Chemistry,2016,vol. 808,p. 12 - 22
[2]Applied Organometallic Chemistry,2019,vol. 33
  • 77
  • [ 98-80-6 ]
  • [ 67665-47-8 ]
Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 6696 - 6700
    Angew. Chem.,2018,vol. 130,p. 6806 - 6810,5
  • 78
  • [ 33543-78-1 ]
  • [ 98-80-6 ]
  • [ 104996-63-6 ]
YieldReaction ConditionsOperation in experiment
38.9% With pyridine; copper diacetate; In 1,2-dichloro-ethane; at 60℃; for 16h;Molecular sieve; [1122] to a mixture of <strong>[33543-78-1]ethyl 1H-imidazole-2-carboxylate</strong> (5 g, 35.7 mmol) and phenylboronic acid (8.7 g, 71.4 mmol) in dce (150 ml) was added Cu(OAc)2 (7.13 g, 39.25 mmol), pyridine (5.64 g, 71.36 mmol, 5.76 ml), 4a° ms (3 g). The mixture was stirred at 60 °C for 16 hours under 02. The reaction mixture was filtered and the filtrate was concentrated. The crude product was purified by silica gel chromatography eluted with petroleum ether: ethyl acetate = 10: 1, 4: 1 to give compound 221a (3 g, 13.9 mmol, yield: 38.9percent) as a yellow solid. Compound 221a: 1H NMR (400mhz, CDCl3 delta 7.43- 7.39 (m, 3h), 7.27 - 7.23 (m, 2h), 7.22 - 7.19 (m, 1h), 7.11 (d, / = 1.0 hz, 1h), 4.22 (q, = 7.2 hz, 2h), 1.24 (t, j = 7.2 hz, 3h).
Reference： [1]Patent: WO2018/64119,2018,A1 .Location in patent: Paragraph 1122
  • 79
  • [ 1006-33-3 ]
  • [ 98-80-6 ]
  • ethyl 3-(4-fluoro-[1,1'-biphenyl]-2-yl)-3-oxopropanoate [ No CAS ]
Reference： [1]Organic Letters,2018,vol. 20,p. 3728 - 3731
  • 80
  • [ 1006-33-3 ]
  • [ 98-80-6 ]
  • C14H11FO [ No CAS ]
Reference： [1]Organic Letters,2018,vol. 20,p. 3728 - 3731
  • 81
  • [ 6292-59-7 ]
  • [ 6000-59-5 ]
  • [ 98-80-6 ]
  • 2-(4-tert-butylphenylsulfonamido)-2-phenylacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In nitromethane; at 60℃; for 12h; General procedure: A 10?mL screw cap glass tube with a PP-cap was charged with a magnetic stirring bar, sulfonamide 1 or 6 (0.25 mmol, 1.0 equiv), glyoxylic acid monohydrate (2; 30.0 mg, 0.33 mmol, 1.3 equiv), phenylboronic acid (3a; 61.0 mg, 0.5 mmol, 2.0 equiv), and nitromethane (1.5 mL, 0.17 M wrt sulfonamide) and firmly closed. The resulting mixture was stirred at 60 °C for 12 h. After cooling to r.t., the mixture was diluted with acetone and filtered through a short plug of Celite/silica gel. The plug was rinsed with additional acetone and the filtrate was concentrated under reduced pressure. Purification of the crude residue by flash column chromatography afforded the product.
Reference： [1]Synthesis,2018,vol. 50,p. 3936 - 3946
  • 82
  • [ 288-88-0 ]
  • [ 98-80-6 ]
  • [ 13423-60-4 ]
Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 8984 - 8988
  • 83
  • [ 57531-37-0 ]
  • [ 98-80-6 ]
  • 2-chloro-4-nitro-1-phenyl-1H-imidazole [ No CAS ]
Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 2134 - 2147
  • 84
  • [ 819-19-2 ]
  • [ 583-53-9 ]
  • [ 98-80-6 ]
  • [ 224311-51-7 ]
YieldReaction ConditionsOperation in experiment
88% Under the protection of argon, a reaction solvent of 1 L of toluene was added to the dry reactor.Then, di-tert-butylphosphine (146 g, 1 mol), o-dibromobenzene (236 g, 1 mol),Bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(0) (6.4 g, 0.01 mol) and sodium carbonate (424 g, 4 mol), Then heat up to 100oC for 6 hours.After the reaction solution is cooled to 20-30oC, phenylboric acid (122 g, 1 mol) is directly added to the system, and then the temperature is raised to 80 ° C for 10 hours; then the reaction is quenched by adding water, and extracted.Drying, after distilling off the solvent under reduced pressure,Recrystallization from methanol gave 262 g of 2-(di-tert-butylphosphine)biphenyl in a yield of 88percent.
Reference： [1]Patent: CN109369715,2019,A .Location in patent: Paragraph 0012
  • 85
  • [ 59237-53-5 ]
  • [ 98-80-6 ]
  • C13H10N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium phosphate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); In tetrahydrofuran; water; at 70℃;Inert atmosphere; 2-Chloro-3-nitropyridine-5-carboxylic acid methyl ester (220 mg, 1 mmol),Phenylboronic acid (146 mg, 1.2 mmol), Pd(dppf)Cl2 (59 mg, 0.08 mmol)And potassium phosphate trihydrate (532mg, 2mmol) was added toTHF (20 mL) and water (4 mL)The mixed solvent was purged with nitrogen and reacted at 70 ° C overnight.Dilute with ethyl acetate (100 mL).Saturated brine(50 mL), the organic phase was dried over anhydrous sodium sulfate and filtered.After concentration, purification by column chromatography(petroleum ether: ethyl acetate = 50:1 to 10:1),Get a white solid(240 mg, 85percent).
Reference： [1]Patent: CN109553617,2019,A .Location in patent: Paragraph 0069; 0070; 0071; 0072; 0073
  • 86
  • [ 34259-99-9 ]
  • [ 98-80-6 ]
  • [ 1826-12-6 ]
Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 12913 - 12924
  • 87
  • [ 52436-73-4 ]
  • [ 98-80-6 ]
  • [ 5707-44-8 ]
YieldReaction ConditionsOperation in experiment
75% With [Pd(2-pyrimidinolate)2]n; In methanol; for 4h;Heating; Green chemistry; General procedure: To an Aryl diazonium salt derivative (1 mmol) and Phenylboronic acid derivative (1.5 mmol) at 25 C was added Pd-MOF (3% mmol) and Methanol (5 ml). The reaction mixture was stirred at 40 C (oil temperature) for 2 he23 h. After cooling to room temperature, the mixture was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to 3a-n, 4a-h. The analytical data of the products are summarized below.
Reference： [1]Tetrahedron,2019,vol. 75
  • 88
  • [ 15294-81-2 ]
  • [ 98-80-6 ]
  • [ 5533-73-3 ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Reflux; 15.38 g (67.79 mmol) of <strong>[15294-81-2]4,5-dibromo-1H-1,2,3-triazole</strong>, 24.80 g (203.38 mmol) of phenylboronic acid, 7.83 g (6.78 mmol) of tetrakis(triphenylphosphine)palladium(0), and 18.74 g (135.59 mmol) of potassium carbonate were added to a mixed solution including 170 mL of tetrahydrofuran and 70 mL of water, and stirred under reflux. After the reaction was completed, the reaction product was cooled to room temperature, and an aqueous solution layer was removed therefrom by extraction. The resultant was filtered under reduced pressure through silica gel, and the filtrate was concentrated under reduced pressure. The product obtained therefrom was separated by silica gel column chromatography to obtain 7.31 g (yield of 49%) of Intermediate (D). (0279) LC-Mass (Calcd: 221.10 g/mol, Found: M+1=222 g/mol)
Reference： [1]Patent: US2019/334095,2019,A1 .Location in patent: Paragraph 0277-0279

Tags: 98-80-6 synthesis path| 98-80-6 SDS| 98-80-6 COA| 98-80-6 purity| 98-80-6 application| 98-80-6 NMR| 98-80-6 COA| 98-80-6 structure

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