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

HRID 1841260Notes

Reaction equation

HRID 1841260 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-8df71e5adccc472f84157f7502a0f77a
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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