Sodium cyanoborohydride → 3-benzyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester

HRID 18173

반응식

HRID 18173 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[Br:23])=[O:5])[CH3:2].[BH3-]C#N.[Na+].CCOC(C)=O.O>ClCCCl.[Zn+2].[I-].[I-]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[Br:23])=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 22728543Water ethylacetateHCID 593449273-benzoyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester

생성물 1

HCID 593449063-benzyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester수율 30.1%

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 3-benzoyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester (2.4 g, 6.45 mmol) in 1,2-dichloroethane (80 ml) was added NaBH3CN (3.24 g, 51.6 mmol) and ZnI2 (6.18 g, 19.4 mmol). After stirring at room temperature for 30 minutes, the reaction mixture was poured into a mixture of EtOAc/H2O. The organic layer was separated and washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting residue was purified by flash chromatography to give 3-benzyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester as yellow solid (696 mg, 30%). 1H NMR (CDCl3, 300 MHz) δ: 1.39 (t, 3H, J=7.13 Hz), 4.43 (q, 2H, J=7.13 Hz), 4.49 (s, 2H), 6.98 (t, 1H, J=7.8 Hz), 7.22 (m, 5H), 7.46 (d, 1H, J=7.60 Hz), 7.54 (d, 1H, J=8.10 Hz).

후처리

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic fraction was concentrated in vacuo
  5. customthe resulting residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-3a11ac495ff34ddc92b9eeca27037eda
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741326B2

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