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Potassium Hydroxide → 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(difluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one

HRID 577478
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HRID 577478 반응식
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([Cl:27])[C:20]([OH:26])=[CH:21][CH:22]=3)[C:17]2=[O:28])=[C:13]([CH3:29])[CH:12]=[C:11]([CH3:30])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Br[C:34](P(=O)(OCC)OCC)([F:36])[F:35]>CC#N.O.CCOC(C)=O.O>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([Cl:27])[C:20]([O:26][CH:34]([F:36])[F:35])=[CH:21][CH:22]=3)[C:17]2=[O:28])=[C:13]([CH3:29])[CH:12]=[C:11]([CH3:30])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

7

반응물 3

HCID 14797Potassium HydroxideHCID 144101Bromodifluoromethyl diethylphosphonateHCID 867237042-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one

생성물 1

HCID 867237052-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(difluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one수율 72%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8857Ethyl Acetate용매
HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

To a solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (1h, 0.1 g, 0.237 mmol) and KOH (0.265 g, 4.74 mmol) in CH3CN/H2O (10 mL/1 mL) was added diethyl [bromo(difluoro)methyl]phosphonate (0.126 g, 0.474 mmol) at −78° C. under N2 atmosphere. The resulting mixture was allowed to warm to room temperature and stirred for 30 minutes. The mixture was diluted with EtOAc (20 mL) and H2O (5 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×10 mL). The organic layers were combined, washed with brine (10 mL), dried over Na2SO4, and concentrated under vacuum. The residue was purified by prep. TLC (petroleum ether/EtOAc, 4:1) to obtain 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(difluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one (1i, 0.08 g, 72%) as a yellow oil.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×10 mL)
  3. washwashed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by prep

출처 및 근거

ORD 기록
ord-610e96a60d7f4cba9a1d75ede5034e86
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040515B2

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