Water → HCID 73426446, compound

HRID 1507599Notes

Reaction equation

HRID 1507599 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].[CH3:23][S:24]([CH:27]=[CH2:28])(=[O:26])=[O:25].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]([CH2:28][CH2:27][S:24]([CH3:23])(=[O:26])=[O:25])[C:3]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 19354Methyl vinyl sulfoneHCID 73426362HCID 73426362, compound

Product 1

HCID 73426446HCID 73426446, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3,3-dimethyl-2-oxoindolin-6-yl)-3-fluoroisonicotinamide (example 72, 100 mg, 334 μmol) in DMF (1.67 ml) under an argon atmosphere was added methylsulfonylethene (35.5 mg, 31.6 μl, 334 μmol) and cesium carbonate (109 mg, 334 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 preparative HPLC. The title compound was obtained as off-white solid (60 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-d476dc16b9774a6f98c2732565baedd7
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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