Dimethylformamide → (6-Fluoro-1H-indol-3-yl)acetonitrile

HRID 1666877Notes

Reaction equation

HRID 1666877 reaction equation
[C-]#N.[K+].CN([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[NH:10][CH:9]=1)C.[CH3:18][N:19](C=O)C>O.C1(C)C=CC=CC=1>[F:17][C:13]1[CH:12]=[C:11]2[C:16]([C:8]([CH2:7][C:18]#[N:19])=[CH:9][NH:10]2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 27744716-Fluorogramine

Product 1

HCID 21071427(6-Fluoro-1H-indol-3-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Combine KCN (50.8 g, 0.78 mol), 3-(N,N-dimethylaminomethyl)-6-fluoroindole (100 g, 0.52 mol), DMF (400 mL) and water (200 mL). Heat to reflux. Evolution of gas begins at about 70° C. Maintain the reflux for 4 hours. Cool the reaction mixture to room temperature, dilute with water and toluene and stir for 10 minutes. Decant the organic layer and wash successively with of saturated aqueous sodium bicarbonate and of 2M aqueous hydrochloric acid. Concentrate to dryness the organic layer to give 2-(6-fluoro-1H-indol-3-yl)acetonitrile.

Workup

  1. temperatureHeat to reflux
  2. custombegins at about 70° C
  3. temperatureMaintain the
  4. temperaturereflux for 4 hours
  5. customDecant the organic layer
  6. washwash successively with of saturated aqueous sodium bicarbonate and of 2M aqueous hydrochloric acid
  7. concentrationConcentrate to dryness the organic layer

Sources & evidence

ORD record
ord-af891ed635584d1f94b392eec2cd3387
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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