Water → HCID 86680487, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1-methylpyridin-2(1H)-one (1.0 g, 5.31 mmol) in 1,4-dioxane (10 mL)\H2O (5 mL) was added 5-acetylthiophen-2-yl boronic acid (1.35 g, 7.97 mmol), tetra-butyl ammonium bromide (17 mg, 0.053 mmol), K2CO3 (2.19 g, 15.93 mmol) and Pd(PPh3)2Cl2 (37 mg, 0.053 mmol) under argon. The mixture was degassed and heated to 100° C. for 3 h. After the reaction was complete based on monitoring by TLC (80% EtOAc\hexane), the mixture was filtered with Celite® reagent and the filtrate was separated. This filtrate was concentrated and extracted with EtOAc (2×100 mL), washed with water (100 mL), and brine solution (100 mL). The organic layer was dried over sodium sulphate and concentrated in vacuum. The residue was purified by Combiflash® column purifier (80% ethyl acetate in hexane) to provide 5-(5-acetylthiophen-2-yl)-1-methylpyridin-2(1H)-one as a yellow viscous liquid (0.65 g, 43% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.31 (d, 1H), 7.88 (d, 1H), 7.80 (dd, 1H), 7.41 (d, 1H), 6.46 (d, 1H), 3.48 (s, 3H), 2.48 (s, 3H); LC-MS m/z calcd for [M+H]+ 234.05. found 234.1.

Provenance & Evidence