Ethanone, 1-(5-bromo-2,3-dihydro-1H-indol-1-yl)-2,2,2-trifluoro- → 1-(2,2,2-Trifluoroacetyl)indoline-5-carbonitrile

HRID 1992338노트

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HRID 1992338 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:6][CH2:5]2.[C:17]([Cu])#[N:18]>CN(C=O)C.O>[F:13][C:12]([F:15])([F:14])[C:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:17]#[N:18])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)=[O:16]

참가 물질

5

반응물 2

HCID 86625990Ethanone, 1-(5-bromo-2,3-dihydro-1H-indol-1-yl)-2,2,2-trifluoro-HCID 178418546HCID 178418546, 화합물

생성물 1

HCID 866259911-(2,2,2-Trifluoroacetyl)indoline-5-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
160 °C

실험 절차

1-(5-Bromo-2,3-dihydro-1H-indol-1-yl)-2,2,2-trifluoroethanone (19 g, 0.0646 mol; see step (ii) above) was dissolved in DMF (50 mL). CuCN (8.68 g, 0.0969 mol) was then added and the reaction mixture was stirred at 160° C. for 4 days, before being cooled to RT, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate then concentrated under reduced pressure. The resulting residue was purified by column chromatography to give the sub-title compound as a white solid. Yield: 13 g.

후처리

  1. temperaturebefore being cooled to RT
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationthen concentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-c396bab42d2443909e0bc05ed2b3885b
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07648985B2

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