Potassium Carbonate → HCID 66696634, compound

Participants

Reaction Steps

A mixture of 5-bromopicolinaldehyde (7.80 g, 41.9 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (8.78 g, 41.9 mmol), and K2CO3 (7.53 g, 54.5 mmol) in MeOH (150 mL) was heated at reflux for 3 hr. The reaction was then cooled to room temperature, the MeOH was evaporated at reduced pressure, and the crude material was partitioned between EtOAc and water. The separated aqueous layer was extracted twice with EtOAc. The combined organic extract was washed twice with water, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel (Analogix® SF65-600 column, 0% to 50% EtOAc/hexane) to afford 7.32 g (73%) of the title compound as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.78 (dd, J=2.4, 0.6, 1H), 8.44 (s, 1H), 8.15 (dd, J=8.5, 2.4, 1H), 7.64 (dd, J=8.5, 0.6, 1H), 2.50 (s, 3H). MS (DCI+) m/z 239/241 (M+H).

Provenance & Evidence