Water → HCID 73426445, compound

HRID 1507598Notes

Reaction equation

HRID 1507598 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[F:19])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:21].FC(F)(F)S(O[CH2:29][C:30]([F:33])([F:32])[F:31])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:1][C:2]1([CH3:22])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[F:19])=[CH:8][CH:9]=2)[N:4]([CH2:29][C:30]([F:33])([F:32])[F:31])[C:3]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 73426362HCID 73426362, compound

Product 1

HCID 73426445HCID 73426445, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3,3-dimethyl-2-oxoindolin-6-yl)-3-fluoroisonicotinamide (example 72, 78 mg, 261 μmol) in DMF (700 μl) under an argon atmosphere was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (66.5 mg, 39.6 μl, 287 μmol) and cesium carbonate (93.4 mg, 287 μmol). After 3 hours at room temperature the reaction mixture was poured into water and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (with 10% ammonia) as eluent followed by trituration with diethyl ether/heptane. The title compound was obtained as white foam (36 mg).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-219a830c901d4d4bb49b8f99e928757b
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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