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

HRID 1851401Notes

Reaction equation

HRID 1851401 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 at room temperature overnight. To the reaction mixture was added water, and the resulting crystals were filtrated, 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 filtrated
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-245984d97159448790c1b81ff3f747be
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…