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

HRID 1992338Notes

Reaction equation

HRID 1992338 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c396bab42d2443909e0bc05ed2b3885b
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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