Cesium carbonate → HCID 67405478, compound
Reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]([F:14])([F:13])[F:12])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]#[N:26]>CN(C=O)C>[C:25]([CH2:24][N:3]1[C:4]2[C:9](=[C:8]([C:11]([F:12])([F:14])[F:13])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])#[N:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.5 g, 2.23 mmol) in DMF (5 mL) was added Cs2CO3 (1.45 g, 4.46 mmol) and bromoacetonitrile (0.54 g, 4.46 mmol). The mixture was heated at 70° C. for 10 min. Additional bromoacetonitrile (0.35 g, 2.9 mmol) was added, and heating was continued for another 10 min. Upon cooling, the mixture was partitioned between Et2O and 0.1N HCl. The organic phase was washed with sat'd brine. The combined aqueous phases were washed with Et2O, and this organic phase was washed with sat'd brine. The combined organic phases were dried (Na2SO4), filtered and concentrated to dryness, to yield a brown solid (0.59 g), which was used in the next step without further purification: LC/MS (ES) shows 87% title compound (m/z 264 (M+1)) and 13% starting material.
Workup
- temperatureheating
- temperatureUpon cooling
- customthe mixture was partitioned between Et2O and 0.1N HCl
- washThe organic phase was washed with sat'd brine
- washThe combined aqueous phases were washed with Et2O
- washthis organic phase was washed with sat'd brine
- dry with materialThe combined organic phases were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-d89d57f82c8d4150b8cac3f2ce35c771
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673948B2
Reaction notes
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