Ethyl Acetate → HCID 91609865, compound

HRID 349231Notes

Reaction equation

HRID 349231 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 91609865HCID 91609865, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-de61020081a244278b14c29da050ce4d
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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