Diisopropylethylamine → 1-(2-Fluoro-4-methanesulfonylphenyl)-2-methyl-1H-imidazole-4-carboxylic acid

HRID 1409734Notes

Reaction equation

HRID 1409734 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1.C(N(CC)C(C)C)(C)C.F[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:21]=1[F:30]>CN(C)C=O>[F:30][C:21]1[CH:22]=[C:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:24]=[CH:25][C:20]=1[N:3]1[CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=[C:2]1[CH3:1]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27827431,2-Difluoro-4-(methylsulfonyl)benzeneHCID 178433052HCID 178433052, compound

Product 1

HCID 710937761-(2-Fluoro-4-methanesulfonylphenyl)-2-methyl-1H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-1H-imidazole-4-carboxylic acid (500 mg), N,N-diisopropyl-ethyl-amine (4 mL), and 1,2-difluoro-4-methanesulfonylbenzene (1.2 g), in N,N-dimethylformamide (6 mL) is heated to 120° C. overnight. The crude product is purified by HPLC. LC (method 20): tR=0.90 min; Mass spectrum (APCI): m/z=299 [M+H]+.

Workup

  1. customThe crude product is purified by HPLC

Sources & evidence

ORD record
ord-67f3a97b89934ddf9a668c8742595daa
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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