Acetic Acid → [1-(3-Bromo-5-fluoro-phenyl)-1H-imidazol-4-yl]-methanol

HRID 1841261Notes

Reaction equation

HRID 1841261 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].C([O:17][CH2:18][CH3:19])(OCC)OCC.[N+:20]([CH2:23]C(OCC)=O)([O-])=O.[C:29](O)(=O)C>[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[CH:29]=[C:19]([CH2:18][OH:17])[N:20]=[CH:23]2)[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 150201553-Bromo-5-fluoroaniline

Product 1

HCID 23445045[1-(3-Bromo-5-fluoro-phenyl)-1H-imidazol-4-yl]-methanol

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 3-bromo-5-fluoroaniline (K. Yoshiizumi et al., Bioorg.Med.Chem.Lett., 1998, 8, 3397-3402) 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. Mp. 134-138° C. (AcOEt/hexane), MS: m/e=271 (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-76423fa7ef8541f5af463d23b13470c0
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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