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

HRID 1930223ノート

反応式

HRID 1930223 の反応式
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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 598182577-bromo-6-fluoro-2-(4-methoxybenzyl)isoquinolin-1(2H)-one

生成物 1

HCID 576525476-Fluoro-2-[(4-methoxyphenyl)methyl]-7-phenylisoquinolin-1(2H)-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-3c5d703e4bab4ad38b412cc2d873d335
出典データセット
uspto-grants-2012_05
特許番号
US08188117B2

反応ノート

読み込み中…