Acetonitrile → Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

HRID 24250

반응식

HRID 24250 반응식
BrCC1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[CH:5][C:4]=1C(C)C.[C:25]([N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(=O)[CH3:26].[C:33]([O-])([O-])=O.[Na+].[Na+].[CH3:39][C:40]#N>O>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]#[C:9][C:6]2[CH:5]=[CH:4][C:25]([N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)=[C:26]([CH:40]([CH3:39])[CH3:33])[C:7]=2[CH3:8])=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 86585936Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate2회

생성물 1

HCID 86585935Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetate수율 58%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate (Intermediate 156, 72.0 mg, 0.19 mmol) and 1-acetylimidazole (22.0 mg, 0.20 mmol) in 5 mL CH3CN was heated at 65° C. for 8 h and then at 55° C. for 16 hours. The solution was cooled to room temperature, diluted with H2O and made basic by addition of Na2CO3, and extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concentrated under reduced pressure. Column chromatography (0.5% Et3N in 5% MeOH-EtOAc) afforded 40.0 mg (58%) of the title compound as a colorless solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0c5327f06f7443058d402b085009dedf
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855512B2

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