Sodium hydride → HCID 18317793, compound

HRID 1700439Notes

Reaction equation

HRID 1700439 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[CH3:20])[CH2:8][C:7]=2[NH:6][CH:5]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)([O-])O.[Na+]>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[CH3:20])[CH2:10][C:11](=[O:13])[C:12]=2[C:4]([CH3:3])=[CH:5]1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 111074403-Methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one

Product 1

HCID 18317793HCID 18317793, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.12 g, washed with hexane thrice) in dimethylformamide (10 ml) was added 3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (0.60 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added a solution of methanesulfonylchloride (0.43 g) in dimethylformamide (3 ml), and the mixture was stirred at the same temperature for 12 hours. To the mixture was added methanesulfonylchloride (0.74 g), and the mixture was stirred for 3 hours. To the mixture was added sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give crystals, which were recrystallized from ethyl acetate-hexane to give colorless crystals of 1-methanesulfonyl-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (0.35 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 12 hours
  2. stirringthe mixture was stirred for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 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. customto give crystals, which
  9. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d4126a7123714386a2993d518d93eb65
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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