Cesium carbonate → HCID 67405478, compound

HRID 2102082Notes

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

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-c56f2be8d33d48d9ad32759eb4520090
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572820B2

Reaction notes

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