Ethanol → 8-Oxa-3-azabicyclo[3.2.1]octan-3-yl(4-(4-chlorophenyl)thiazol-2-yl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-oxa-3-azabicyclo[3.2.1]octan-3-yl(4-bromothiazol-2-yl)methanone (Step-1 of compound 67, 1.1 g, 3.63 mmol) in a mixture of toluene:ethanol (5 ml:15 ml) were added (4-chlorophenyl) boronic acid (0.85 g, 5.44 mmol) and potassium carbonate (1.25 g, 9.07 mmol) at 25° C. in a tube, the nitrogen gas was bubbled through reaction mixture for 15 minutes. To the reaction mixture was added tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.36 mmol) under nitrogen and the tube was sealed. The reaction mixture was heated at 90-95° C. for 18 hr with stirring. The progress of reaction was monitored by TLC; the reaction mixture was cooled to 25° C. and filtered through celite. The residue was washed with mixture of 10% methanol in dichloromethane (2×50 ml). The filtrate was concentrated under reduced pressure to obtain a crude product; which was purified by column chromatography over silica gel (100-200 mesh) using 25% ethyl acetate in hexanes as an eluent to obtain the title compound (0.7 g, 57.8%). MS: m/z 335 (M+1).

Provenance & Evidence