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Ethyl Acetate → 2-Bromo-5-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-yl-methoxy}-pyrazine

HRID 349231
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인쇄 미리보기

반응식

HRID 349231 반응식
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:6][CH:7]=1.[Br:20][C:21]1[N:22]=[CH:23][C:24]([OH:27])=[N:25][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[Br:20][C:21]1[CH:26]=[N:25][C:24]([O:27][CH2:2][C:3]2[N:4]=[C:5]([CH:8]=[CH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)[O:6][CH:7]=2)=[CH:23][N:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 690682904-Chloromethyl-2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazoleHCID 178516739HCID 178516739, 화합물

생성물 1

HCID 916098652-Bromo-5-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-yl-methoxy}-pyrazine

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

A mixture of 4-chlormethyl-2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazole (0.345 g, 1.2 mmol), 5-bromo-pyrazin-2-ol (0.175 g, 1.0 mmol) and cesium carbonate (Cs2CO3) (0.489 g, 1.5 mmol) in DMF (4 ml) is kept at 80° C. for 1 h. After cooling ethyl acetate (40 ml) is added, the mixture is washed with sat. NH4Cl and brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/hexane 1:9->ethyl acetate/hexane 1:2) yielding 2-bromo-5-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-yl-methoxy}-pyrazine as a white solid. Yield 122 mg (29%).

후처리

  1. additionis added
  2. washthe mixture is washed with sat. NH4Cl and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash column chromatography (ethyl acetate/hexane 1:9->ethyl acetate/hexane 1:2)

출처 및 근거

ORD 기록
ord-de61020081a244278b14c29da050ce4d
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07179812B2

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