Dimethylformamide → HCID 57901725, compound

HRID 1851600Notes

Reaction equation

HRID 1851600 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[C:12]([CH3:25])[C:13]([CH3:24])=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15]2)(=[O:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:37](I)[CH3:38]>C(OCC)(=O)C>[CH2:37]([N:9]([S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:7])=[O:8])[C:10]1[CH:11]=[C:12]([CH3:25])[C:13]([CH3:24])=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15]2)[CH3:38]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 57901832HCID 57901832, compound

Product 1

HCID 57901725HCID 57901725, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 7-[(2-thienylsulfonyl)amino]-4,5-dimethyl-1H-indole-2-carboxylate (0.35 g), potassium carbonate (0.13 g) and N,N-dimethylformamide (8 mL) was added dropwise ethyl iodide (0.074 mL) under ice-cooling. The mixture was stirred at from under ice-cooling to room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-2:8), and the obtained colorless crystals were recrystallized from ethyl acetate-hexane to give the title compound (253 mg, yield 67%) as colorless prism crystals. melting point 134-135° C.

Workup

  1. temperaturecooling
  2. washwashed successively with aqueous citric acid solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained colorless crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-27be8b4a4689451fb4a806b983916648
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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