Formamide → 4-(4-Bromo-3,5-dimethoxyphenyl)-5-methyloxazole

Reaction equation

Br[CH:2]([CH3:16])[C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([Br:13])=[C:7]([O:14][CH3:15])[CH:6]=1)=O.CCOC(C)=O.C([O-])(O)=O.[Na+].[CH:28]([NH2:30])=[O:29]>>[Br:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:5]([C:3]2[N:30]=[CH:28][O:29][C:2]=2[CH3:16])=[CH:6][C:7]=1[O:14][CH3:15]

Participants

Reactant 4

HCID 713Formamide

HCID 8857Ethyl Acetate

HCID 516892Sodium Bicarbonate

HCID 584320252-Bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one

Product 1

HCID 584319854-(4-Bromo-3,5-dimethoxyphenyl)-5-methyloxazoleYield 55%

Procedure

A solution of 2-bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one (1.07 g, 3.04 mmol) in formamide (10 mL) in an oven-dried flask under argon was heated at 110° C. for 16 hrs. After cooling to room temp, EtOAc and saturated aqueous NaHCO3 were carefully added and the mixture was stirred for 15 minutes. It was then extracted with EtOAc twice and the combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated. Purification by chromatography (30% EtOAc-hexanes) gave 4-(4-bromo-3,5-dimethoxyphenyl)-5-methyloxazole as a yellow solid (0.496 g, 55% yield).