Cesium carbonate → 1-(Cyanomethyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 2101870Notes

Reaction equation

HRID 2101870 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:11]([C:12]#[N:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][C:24]#[N:25]>CN(C=O)C>[C:24]([CH2:23][N:7]1[C:8]2[C:4](=[C:3]([C:2]([F:14])([F:1])[F:15])[C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1)#[N:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 674054494-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 249838341-(Cyanomethyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrileYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To 4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.210 g, 1.00 mmol) in DMF (20 mL), was added Cs2CO3 (0.489 g, 1.50 mmol) and bromoacetonitrile (0.180 g, 1.50 mmol). The reaction mixture was heated at 75° C. under an N2 atmosphere for 1 hr. Dilution with water was followed by extraction with Et2O. The combined organic portions were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification (SiO2, EtOAc/hexanes) afforded 0.211 g of the title compound: MS (ESI): m/z 250 (M+1).

Workup

  1. extractionDilution with water was followed by extraction with Et2O
  2. washThe combined organic portions were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-2f8be1fa4ca040ad8eaf70e063a252de
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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