Sodium hydride → Ethyl 1-(cyanomethyl)-6-methoxy-1H-indole-2-carboxylate

HRID 1675338

반응식

HRID 1675338 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[Cl-].[C:20](#[N:22])[CH3:21]>CN(C)C=O>[C:20]([CH2:21][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH:7]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:22]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 612959Ethyl 6-methoxy-1H-indole-2-carboxylateHCID 21844797Acetonitrile chloride

생성물 1

HCID 67331182Ethyl 1-(cyanomethyl)-6-methoxy-1H-indole-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Under nitrogen, dissolve 2.15 g of ethyl 6-methoxy-1H-indole-2-carboxylate in 10 ml of dimethylformamide. Add 0.59 g of sodium hydride in small portions at 0° C. and stir the reaction at 0° C. for 30 minutes. Add 0.93 ml of acetonitrile chloride at 0° C. and stir the reaction at ambient temperature for 24 hours. Add water and extract with ethyl acetate. Wash the organic phase with saturated aqueous sodium hydrogen carbonate solution and with saturated aqueous sodium chloride solution. Dry the organic phase over sodium sulfate, filter and evaporate. Purify the compound by column chromatography on silica gel using dichloromethane as eluant. The title compound is obtained in the form of a white powder.

후처리

  1. customthe reaction at 0° C. for 30 minutes
  2. stirringstir
  3. customthe reaction at ambient temperature for 24 hours
  4. extractionAdd water and extract with ethyl acetate
  5. washWash the organic phase with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialDry the organic phase over sodium sulfate
  7. filtrationfilter
  8. customevaporate
  9. customPurify the compound by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-52cb79800106468da5f87f8a9544c8a8
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003682B2

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