Methyl iodide → ethyl 7-(methyl{[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate

HRID 1960358Notes

Reaction equation

HRID 1960358 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18]2)(=[O:11])=[O:10].[C:29](=O)([O-])[O-].[K+].[K+].CI.CCCCCC>CN(C)C=O.C(OCC)(=O)C>[CH3:29][N:12]([S:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:27])([F:1])[F:28])(=[O:11])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18]2

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 8058HexaneHCID 11430Potassium CarbonateHCID 57476178ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate

Product 1

HCID 59135580ethyl 7-(methyl{[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate (5.0 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (50 mL) was added methyl iodide (0.75 mL) under ice-cooling, and the mixture was stirred from under ice-cooling to room temperature for 18 hr. The reaction solution was ice-cooled, methyl iodide (0.75 mL) was added again, and the mixture was stirred from under ice-cooling to room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed with water, aqueous citric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to basic silica gel column chromatography (ethyl acetate:hexane=20:80-35:65), and the obtained crude product was subjected three times to silica gel column chromatography (ethyl acetate:hexane=5:95-10:90) to give the title compound (3.7 g, yield: 72%) as a pale-yellow oil. MS: 427(MH+).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringthe mixture was stirred from under ice-
  4. temperaturecooling to room temperature for 18 hr
  5. washwashed with water, aqueous citric acid solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained crude product

Sources & evidence

ORD record
ord-51116be006b84136b6a50f03bf76aff3
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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