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

HRID 18173

反応式

HRID 18173 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 111,2-Dichloroethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3a11ac495ff34ddc92b9eeca27037eda
出典データセット
uspto-grants-2010_06
特許番号
US07741326B2

関連ノート

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