Potassium Carbonate → 6-Fluoro-2-[(4-methoxyphenyl)methyl]-7-phenylisoquinolin-1(2H)-one

HRID 1930223Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:9]2=[O:12])=[CH:4][C:3]=1[F:22].C([O-])([O-])=O.[K+].[K+].[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[F:22][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:9](=[O:12])[N:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH:7]=[CH:6]2

Participants

Conditions

Temperature: 100 °C

Procedure

453 mg (1.25 mmol) 7-bromo-6-fluoro-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (313), 432 mg (3.125 mmol) K2CO3 and 190.5 mg (1.56 mmol) phenylboronic acid were dissolved in 12.5 mL toluene. Under Argon, 72 mg (0.062 mmol) Pd(Ph3)4 were added and the solution was stirred at 100° C. After complete conversion, the solvent is removed i. vac. and saturated sodium bicarbonate solution is added. The aqueous solution is extracted three times with dichloromethane and the organic layers are dried with MgSO4. After evaporation, the crude product is purified by preparative HPLC. Rt=1.80 min (Method C). Detected mass: 360.4 (M+H+).

Workup

customAfter complete conversion, the solvent is removed i
additionand saturated sodium bicarbonate solution is added
extractionThe aqueous solution is extracted three times with dichloromethane
dry with materialthe organic layers are dried with MgSO4
customAfter evaporation
customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record: ord-3c5d703e4bab4ad38b412cc2d873d335
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188117B2

Reaction notes

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