Sodium hydride → 1-Methanesulfonyl-3-methyl-6-(2-fluorophenyl)-4,5,6,7-tetrahydroindol-4-one

HRID 1700441Notes

Reaction equation

HRID 1700441 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:11](=[O:13])[CH2:10][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[CH2:8][C:7]=2[NH:6][CH:5]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>CN(C)C=O>[CH3:21][S:22]([N:6]1[C:7]2[CH2:8][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[CH2:10][C:11](=[O:13])[C:12]=2[C:4]([CH3:3])=[CH:5]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 183173603-Methyl-6-(2-fluorophenyl)-4,5,6,7-tetrahydroindol-4-one

Product 1

HCID 183175421-Methanesulfonyl-3-methyl-6-(2-fluorophenyl)-4,5,6,7-tetrahydroindol-4-oneYield 44.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.16 g, washed with hexane thrice) in dimethylformamide (10 ml) was added 3-methyl-6-(2-fluorophenyl)-4,5,6,7-tetrahydroindol-4-one (0.80 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added methanesulfonylchloride (0.41 g) in dimethylformamide (3 ml), and the mixture was stirred at the same temperature for 14 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The mixture was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane), and the resulting crystals were recrystallized from ethyl acetate-hexane to give colorless crystals of 1-methanesulfonyl-3-methyl-6-(2-fluorophenyl)-4,5,6,7-tetrahydroindol-4-one (0.47 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 14 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe mixture was washed with sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (EtOAc/hexane)
  8. customthe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f94c8e724ed647c69ff385b0f20cfe40
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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