Chloroacetonitrile → 4-bromo-1-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester

HRID 853041ノート

反応式

HRID 853041 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[C:14]([Br:17])[CH:13]=[CH:12][CH:11]=2)=[O:7])[CH3:4].Cl[CH2:19][C:20]#[N:21]>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:19][C:20]#[N:21])[C:10]2[C:15]([CH:16]=1)=[C:14]([Br:17])[CH:13]=[CH:12][CH:11]=2)=[O:7])[CH3:4]

参加物

5

反応物 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 10989255Ethyl 4-bromo-1H-indole-2-carboxylate

生成物 1

HCID 694154234-bromo-1-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester収率 71.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Sodiumhydride (4.0 g, 92 mmol) was suspended in dimethylformamide (20 mL) and a solution of 4-bromo-1H-Indole-2-carboxylic acid ethyl ester (16.4 g, 61 mmol) in dimethylformamide (70 mL) was added. The mixture was stirred for 1 h at room temperature and after cooling to 0° C. chloroacetonitrile (7.7 mL, 122 mmol) was added. After 1 h at room temperature the mixture was added to an ice/water mixture (800 mL) and extracted with ethylacetate. The organic phases were pooled washed with brine, dried with MgSO4 and the solvent was removed in vacuo. Chromatography on silica gel (ethyl acetate/n-hexane 4:1) yielded 4-bromo-1-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester (13.4 g, 71%) as a colorless solid, MS: m/e=306.0 (M+).

後処理

  1. additionwas added
  2. extractionextracted with ethylacetate
  3. washThe organic phases were pooled washed with brine
  4. dry with materialdried with MgSO4
  5. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-0a56b83faa7d46ebbfa9f9a3fa37c3d6
出典データセット
uspto-grants-2007_08
特許番号
US07253281B2

反応ノート

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