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

HRID 1930223노트

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HRID 1930223 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-3c5d703e4bab4ad38b412cc2d873d335
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188117B2

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