Dimethylformamide → 2-[6-chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N,N-dimethyl-acetamide

HRID 505072노트

반응식

HRID 505072 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:19][N:20]([CH2:22][C:23](Cl)=O)[CH3:21].CN(C=[O:30])C>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[CH:7][N:8]2[CH2:23][C:22]([N:20]([CH3:21])[CH3:19])=[O:30])=[CH:4][CH:3]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 70103442-(Dimethylamino)acetyl chlorideHCID 224972521-(6-Chloro-3-indolyl)-2,2,2-trifluoroethanone

생성물 1

HCID 667442552-[6-chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N,N-dimethyl-acetamide수율 61%

실험 절차

To a stirred solution of 1-(6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (0.75 g) in 20 ml of DMF at 0° C., were added 128 mg (1.1 eq.) of NaH (60% in oil). The mixture was stirred for 30 min. and then 0.32 ml (1.1 eq.) of dimethylamino-acetyl chloride were added. The mixture was stirred an additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo to afford 598 mg (61%) of 2-[6-chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N,N-dimethyl-acetamide as a white solid.

후처리

  1. stirringThe mixture was stirred an additional hour
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8c3e4cdfe69f4f969f4afd9d75cd167c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781436B2

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