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

HRID 1841262Notes

Reaction equation

HRID 1841262 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-4b41f995c63f4ed3b04ca2053b77d093
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

Loading…