Dimethylformamide → 4-(4-{2-butyl-1-[4-(4-fluoro-3-trifluoromethyl-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-1-methyl-piperidine

HRID 901647

반응식

HRID 901647 반응식
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17].[CH3:20][N:21]([CH:23]=O)[CH3:22].Br[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=O>O.CCOCC>[CH2:9]([C:10]1[N:11]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:14]=[CH:15][C:2]([F:1])=[C:3]([C:16]([F:17])([F:18])[F:19])[CH:4]=3)=[CH:13][CH:12]=2)[CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([O:6][CH:5]3[CH2:14][CH2:22][N:21]([CH3:20])[CH2:23][CH2:4]3)=[CH:31][CH:30]=2)[N:11]=1)[CH2:8][CH2:7][CH3:13]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 6259Phenacyl bromideHCID 669773444-[4-Fluoro-3-(trifluoromethyl)phenoxy]aniline

생성물 1

HCID 596993654-(4-{2-butyl-1-[4-(4-fluoro-3-trifluoromethyl-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-1-methyl-piperidine

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

To a stirred solution of 4-(4-fluoro-3-trifluoromethyl-phenoxy)-aniline (1.64 mmol) in anhydrous DMF (30 mL) DIEA (3 eq) was added, followed by slow addition of the alpha-bromoacetophenone described above (2 eq), according to General Procedure R2. The reaction mixture was stirred under nitrogen at rt until completion, as indicated by TLC and HPLC. The reaction mixture was then diluted with cold H2O and the product was isolated in Et2O. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was purified by chromatography on silica gel (elution with 5–20% EtOAc/Hexane).

후처리

  1. washThe combined organic layers were washed with brine
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of solvent in vacuuo

출처 및 근거

ORD 기록
ord-baf314a250104332a8a57cae2acddab2
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361678B2

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