Methanol → Ethyl 8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

Participants

Reaction Steps

Compound 5b (8.6 g, 28 mmol) was suspended in THF (100 mL)/MeOH (50 mL). The reaction mixture was purged with argon, and 10% Pd/C (1.5 g, 1.4 mmol) was added followed by solid ammonium formate (8.7 g, 140 mmol). The reaction mixture was stirred under reflux for 1 h, during which time some of the ammonium formate sublimed onto the reflux condenser. The solid was rinsed back into the reaction flask with dry MeOH. The reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was concentrated in vacuo to obtain a solid, which was dissolved in DCM (200 mL), and washed with water (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give compound 5c as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.34 (s, 1H), 8.04 (d, J=5.6 Hz, 1H), 6.06 (d, J=5.6 Hz, 1H), 4.43 (q, J=7.1 Hz, 2H), 3.98-4.07 (m, 4H), 3.88-3.96 (m, 4H), 1.42 (t, J=7.1 Hz, 3H).

Provenance & Evidence