Acetic Acid → [1-(3-Difluoromethyl-phenyl)-1H-imidazol-4-yl]-methanol

HRID 433629Notes

Reaction equation

HRID 433629 reaction equation
[F:1][CH:2]([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].C([O:18][CH2:19][CH3:20])(OCC)OCC.[N+:21]([CH2:24]C(OCC)=O)([O-])=O.[C:30](O)(=O)C>[Fe]>[F:1][CH:2]([F:10])[C:3]1[CH:4]=[C:5]([N:6]2[CH:30]=[C:20]([CH2:19][OH:18])[N:21]=[CH:24]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 234451193-(Difluoromethyl)aniline

Product 1

HCID 23444991[1-(3-Difluoromethyl-phenyl)-1H-imidazol-4-yl]-methanol

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 3-difluoromethylaniline (G. E. Wright et al., J. Med. Chem., 1995, 38, 49-57) was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex followed by hydrolytic workup and the title compound was obtained as a light brown solid. MS: m/e=225 (M+H+).

Workup

  1. customThe isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex

Sources & evidence

ORD record
ord-f9b9baed38d34c16a7d3aea4e6f37954
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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