4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER

Under an argon atmosphere, To the reaction vessel, 1.4 mg (0.005 mmol) of dichlorobis (trimethylphosphine) nickel, 77.4 mg (0.5 mmol) of 4-chlorobenzamide, 152 mg (1.0 mmol) of cesium fluoride, 140 mg (0.55 mmol) of 4, 4, 5, 5, 4 ', 4', 5 ', 5'-octamethyl-2, 2'-bi (1, 3, 2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2, 2, 2-trifluoroethoxy) silane and 0.5 mL of 1, 4-dioxane were added and sealed, And the mixture was stirred at 100 ° C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 4: 1: 0 to 4: 1: 1)92 mg (white solid, yield 75percent) of 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzamide was obtained.A mixture of 2-70 (1.0 g, 5 mmol), (PinB)2 (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 mL) was degassed with N2 and stirred at 95 °C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified via column chromatography on silica gel eluting with DCM/MeOH from 20/1 to 10/1 to give intermediate 2-71 (yellow solid, 975 mg, 79percent yield). LCMS (m/z):248 [M+Hj .Step 1Under an argon atmosphere, To the reaction vessel, 1.4 mg (0.005 mmol) of dichlorobis (trimethylphosphine) nickel, 77.4 mg (0.5 mmol) of 4-chlorobenzamide, 152 mg (1.0 mmol) of cesium fluoride, 140 mg (0.55 mmol) of 4, 4, 5, 5, 4 ', 4', 5 ', 5'-octamethyl-2, 2'-bi (1, 3, 2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2, 2, 2-trifluoroethoxy) silane and 0.5 mL of 1, 4-dioxane were added and sealed, And the mixture was stirred at 100 ° C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 4: 1: 0 to 4: 1: 1)92 mg (white solid, yield 75percent) of 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzamide was obtained.A mixture of 2-70 (1.0 g, 5 mmol), (PinB)2 (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 mL) was degassed with N2 and stirred at 95 °C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified via column chromatography on silica gel eluting with DCM/MeOH from 20/1 to 10/1 to give intermediate 2-71 (yellow solid, 975 mg, 79percent yield). LCMS (m/z):248 [M+Hj .Step 1

Molecular Weight:247.10
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:247.1379736
Monoisotopic Mass:247.1379736
Topological Polar Surface Area:61.6
Heavy Atom Count:18
Complexity:319
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes