Acetic Acid → [1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-1H-imidazol-4-yl]-methanol

HRID 433631Notes

Reaction equation

HRID 433631 reaction equation
[F:1][C:2]1([F:12])[O:6][C:5]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:4]=2[O:3]1.C([O:20][CH2:21][CH3:22])(OCC)OCC.[N+:23]([CH2:26]C(OCC)=O)([O-])=O.[C:32](O)(=O)C>[Fe]>[F:12][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH:32]=[C:22]([CH2:21][OH:20])[N:23]=[CH:26]3)=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 27368935-Amino-2,2-difluoro-1,3-benzodioxole

Product 1

HCID 23445088[1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-1H-imidazol-4-yl]-methanol

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 2,2-difluoro-benzo[1,3]dioxol-5-ylamine 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. 163-164° C. (H2O), MS: m/e=254 (M+).

Workup

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

Sources & evidence

ORD record
ord-2ac297953db6476b92c7922ceb60d9f8
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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