Thiazole → 2-Biphenyl-4-yl-1-(1,3-thiazol-2-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

2.0 M of Isopropylmagnesium chloride in tetrahydrofuran (0.24 mL) was added to a solution of 1,3-thiazole (40 mg, 0.47 mmol) in tetrahydrofuran (6 mL) at −78° C. The reaction was stirred for 1 h. as it was warmed to −10° C. 2-Biphenyl-4-yl-N-methoxy-N-methylacetamide (100 mg, 0.4 mmol) in Tetrahydrofuran (2 mL) was added dropwise at −10° C. The reaction was stirred for 2 h. while the reaction was warmed to r.t. gradually. The reaction was quenched with saturated NH4Cl, and was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) gave the 2-biphenyl-4-yl-1-(1,3-thiazol-2-yl)ethanone (70 mg, 60%) as a white solid. Analytical LCMS (M+H)+: m/z=279.9.

Provenance & Evidence