Sodium Carbonate → HCID 86680620, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(5-bromopyridin-2-yl)ethanone (0.5 g, 2.5 mmol) in toluene (10 mL) and ethanol (5 mL) was added furan-3-ylboronic acid (0.335 g, 3.0 mmol) and a 2 M solution of aq. Na2CO3. The reaction mixture was degassed with argon, Pd(PPh3)4 (0.144 g, 0.125 mmol) was added, the reaction mixture was degassed with argon for 10 min, and the reaction was heated to 100° C. for 4 h. The reaction mixture was evaporated under vacuum to remove the ethanol, diluted with water (30 mL), extracted with ethyl acetate (100 mL), dried over sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was purified by Biotage Isolera® One column (using 10% ethyl acetate and hexane) to give 1-(5-(furan-3-yl)pyridin-2-yl)ethanone (0.35 g, 74% yield); 1H NMR (400 MHz, DMSO-d6): δ 9.00 (s, 1H), 8.44 (s, 1H), 8.20-8.17 (m, 1H); 7.95 (d, 1H), 7.83 (s, 1H), 7.13 (s, 1H), 2.57 (s, 3H): LC-MS m/z calcd for [M+H]+ 187.06. found 188.0.

Provenance & Evidence