Dimethylformamide → HCID 9889239, compound

HRID 1814093Notes

Reaction equation

HRID 1814093 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)=[CH:8]2)(=[O:4])=[O:3].CN(C)C=O.[H-].[Na+].[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(OCC)(=O)C>[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([N:10]2[C:11]3[C:7](=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:13][CH:12]=3)[CH:8]=[C:9]2[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 95884-Fluorobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 15486858HCID 15486858, compound

Product 1

HCID 9889239HCID 9889239, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-methanesulfonyl-2-(thiazol-2-yl)indole (50 mg) and N,N-dimethylformamide (1.8 ml), 60% sodium hydride (10 mg) was added at 0° C. and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture was added 4-fluorobenzenesulfonyl chloride (52 mg) at 0° C. and the mixture was stirred at 15 to 30° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous NaCl solution successively, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 77 mg of the desired product in a white amorphous form.

Workup

  1. additionwas added at 0° C.
  2. stirringthe mixture was stirred at 15 to 30° C. for 1 hour
  3. washwashed with a saturated aqueous sodium hydrogencarbonate solution, water
  4. dry with materiala saturated aqueous NaCl solution successively, dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1bc11c359ee40d5af7669e7a52cd672
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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