1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester → 1-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester

HRID 1481187노트

반응식

HRID 1481187 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Br)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[C:24]([Cu])#[N:25]>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4]

참가 물질

5

반응물 2

HCID 865954711-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl esterHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 898128781-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester수율 24.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 1-bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester (0.91 g, prepared according to Arend et al. WO 2004108681) and CuCN (436 mg) in DMF (5 mL) was refluxed for 1 h; then cooled, diluted with DCM, filtered, then washed with water, dil. NaCl solution, dried over sodium sulphate, filtered, concentrated, the residue was column purified to give the desired product (195 mg). LC MS ESI: 337 (M+1)+.

후처리

  1. temperaturewas refluxed for 1 h
  2. temperaturethen cooled
  3. filtrationfiltered
  4. washwashed with water, dil. NaCl solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified

출처 및 근거

ORD 기록
ord-baaa232e9f2e4518a02a538bc0201b79
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

반응 노트

불러오는 중…