Dimethylformamide → HCID 57476200, compound

HRID 1960386Notes

Reaction equation

HRID 1960386 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)(=[O:21])=[O:20])[CH:17]=1)[NH:14][C:13]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:12]2)(=[O:4])=[O:3].[C:33](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>O>[CH3:33][N:18]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)(=[O:21])=[O:20])[C:16]1[CH:17]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=[C:11]2[C:15]=1[NH:14][C:13]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:12]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57476199HCID 57476199, compound

Product 1

HCID 57476200HCID 57476200, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 5-[3-(methylsulfonyl)propoxy]-7-[(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylate (3.50 g), potassium carbonate (1.01 g) and N,N-dimethylformamide (50 mL) was added methyl iodide (1.14 g) at 0° C., and the reaction mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with a mixed solvent of ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to basic silica gel column chromatography, and eluted with hexane-ethyl acetate (1:1-1:4, volume ratio) to give the title compound (2.70 g, yield 75%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give colorless prism crystals. melting point 176-177° C.

Workup

  1. extractionthe mixture was extracted with a mixed solvent of ethyl acetate-tetrahydrofuran
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. washeluted with hexane-ethyl acetate (1:1-1:4, volume ratio)

Sources & evidence

ORD record
ord-61ac546824a54ae4a1ac1801c026a7a1
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

Loading…