Dimethylformamide → ethyl 4-chloro-1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

HRID 2238894Notes

Reaction equation

HRID 2238894 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:6]2[CH2:20][O:21][CH3:22].CI.[C:30](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:30])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:6]2[CH2:20][O:21][CH3:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57476019ethyl 4-chloro-1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 57476020ethyl 4-chloro-1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylateYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4-chloro-1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (1.14 g), methyl iodide (0.33 ml), potassium carbonate (0.37 g) and N,N-dimethylformamide (10 ml) was stirred overnight at room temperature. Water was added to the reaction mixture, and the resulting crystals were collected by filtration, washed with water, and dried to give the title compound (1.10 g, yield 93%) as colorless crystals. melting point 137-138° C.

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-baf1ef4db9714fe2b8c3b03ac02d6c6a
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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