Sodium hydride → 6-chloro-1-(cyano-methyl-methyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 853044노트

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HRID 853044 반응식
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([Cl:17])[CH:11]=2)=[O:7])[CH3:4].Br[CH:19]([CH3:22])[C:20]#[N:21]>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH:19]([C:20]#[N:21])[CH3:22])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([Cl:17])[CH:11]=2)=[O:7])[CH3:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 1405382-BromopropionitrileHCID 7015027Ethyl 6-chloroindole-2-carboxylate

생성물 1

HCID 694143026-chloro-1-(cyano-methyl-methyl)-1H-indole-2-carboxylic acid ethyl ester수율 83.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

Sodiumhydride (0.89 g, 20.1 mmol) was suspended in dimethylformamide (15 mL) and a solution of 6-chloro-1H-indole-2-carboxylic acid ethyl ester (2.00 g, 8.9 mmol) in dimethylformamide (8 mL) was added at 0° C. The mixture was stirred for 1 h at 0° C. then 2-bromo-propionitrile (3.6 g, 23.95 mmol) was added. After 1 h at room temperature the mixture was heated at 75° C. for 18 hours. The reaction mixture was then added to an ice/water mixture (100 mL) and extracted with ethylacetate. The organic phases were pooled washed with brine, dried with Na2SO4 and the solvent was removed in vacuo. Chromatography on silica gel (ether/n-hexane 1:4) yielded 6-chloro-1-(cyano-methyl-methyl)-1H-indole-2-carboxylic acid ethyl ester (2.06 g, 67%) as a colorless solid, MS: m/e=277.2 (M+H+).

후처리

  1. temperatureAfter 1 h at room temperature the mixture was heated at 75° C. for 18 hours
  2. extractionextracted with ethylacetate
  3. washThe organic phases were pooled washed with brine
  4. dry with materialdried with Na2SO4
  5. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-51b73faeda354cc4b2ede80b96b61208
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253281B2

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