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

HRID 853041노트

반응식

HRID 853041 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-0a56b83faa7d46ebbfa9f9a3fa37c3d6
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253281B2

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