Bromoacetonitrile → diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate

HRID 1710447노트

반응식

HRID 1710447 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]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=2)=[O:7])[CH3:4].Br[CH2:23][C:24]#[N:25]>CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:23][C:24]#[N:25])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=2)=[O:7])[CH3:4]

참가 물질

5

반응물 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate

생성물 1

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A mixture of 60% NaH in mineral oil (115 mg, 2.9 mmol) and 1H-indole-2,6-dicarboxylic acid diethyl ester (500 mg, 1.9 mmol) in DMF (3 mL) was stirred at room temperature for 0.5 h. Then bromo-acetonitrile in DMF (1 mL) was added and the reaction was warmed to 77° C. and kept at this temperature overnight. The reaction was cooled and quenched with ice water. A large amount of precipitate formed which was filtered and rinsed with water, followed by cold ether. The wet cake was dried in the vacuum oven (50° C.) to give 585 mg of 1-cyanomethyl-1H-indole-2,6-dicarboxylic acid diethyl ester.

후처리

  1. temperaturethe reaction was warmed to 77° C.
  2. customkept at this temperature overnight
  3. temperatureThe reaction was cooled
  4. customquenched with ice water
  5. customA large amount of precipitate formed which
  6. filtrationwas filtered
  7. washrinsed with water
  8. customThe wet cake was dried in the vacuum oven (50° C.)

출처 및 근거

ORD 기록
ord-8a8bda555c114889991e7aa0b6747193
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790712B2

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