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

HRID 1992338ノート

反応式

HRID 1992338 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c396bab42d2443909e0bc05ed2b3885b
出典データセット
uspto-grants-2010_01
特許番号
US07648985B2

反応ノート

読み込み中…