Acetic Acid → {1-[3-(1,1-Difluoro-ethyl)-phenyl]-1H-imidazol-4-yl}-methanol

HRID 1841241노트

반응식

HRID 1841241 반응식
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([F:4])[CH3:3].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C([O:46][CH2:47][CH3:48])(OCC)OCC.[N+:49]([CH2:52]C(OCC)=O)([O-])=O.[C:58](O)(=O)C>[Fe]>[F:1][C:2]([C:5]1[CH:6]=[C:7]([N:8]2[CH:58]=[C:48]([CH2:47][OH:46])[N:49]=[CH:52]2)[CH:9]=[CH:10][CH:11]=1)([F:4])[CH3:3]

참가 물질

7

반응물 5

HCID 176Acetic Acid2회HCID 31214Ethyl orthoformate2회HCID 69379Ethyl nitroacetateHCID 180504Ceric ammonium nitrateHCID 234450923-(1,1-Difluoroethyl)aniline

생성물 1

HCID 23445191{1-[3-(1,1-Difluoro-ethyl)-phenyl]-1H-imidazol-4-yl}-methanol

시약·촉매·용매 1

HCID 23925Iron촉매

실험 절차

Following the general method described in example 293, 3-(1,1-difluoro-ethyl)-aniline [R. O. Neri, J. G. Topliss, Ger. Offen. (1972), DE 2130452 19721221 CAN 78:124310]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 white crystalline solid. Mp. 104-108° C. (H2O), MS: m/e=238 (M+).

후처리

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

출처 및 근거

ORD 기록
ord-2f176982b27c49df9e2e20cbd5e2f803
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06683097B2

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