N-bromobutanimide → 7-Benzyl-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

HRID 1481208노트

반응식

HRID 1481208 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[Br:23]N1C(=O)CCC1=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:23])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 671101307-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

생성물 1

HCID 866170717-Benzyl-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 7-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (302 mg, 1.03 mmole, prepared according to procedures in U.S. Pat. No. 7,928,120 B2 for example 22c) and N-bromosuccinimide (202 mg, 1.13 mmole) in anhydrous dichloromethane (5 ml) was stirred at room temperature for twenty hours before it was quenched with water, extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, concentrated and purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a white solid (259 mg). LC-MS ESI+: 372, 374 (79Br/81Br) (M+1)+; ESI−: 370, 372 (79Br/81Br) (M-b) 7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

후처리

  1. customprepared
  2. customwas quenched with water
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-a14347ff4d85452b9ae95e50f674165f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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