Sodium Carbonate → HCID 71526079, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (0.10 g, 0.304 mmol), o-tolylboronic acid (0.045 g, 0.335 mmol), Pd2(dba)3 (0.017 g, 0.03 mmol), X-phos (0.029 g, 0.06 mmol) and Na2CO3 (0.097 g, 0.912 mmol) in dioxane (20 mL) and water (5 mL) was heated to 100° C. for 16 h in a sealed tube under N2 atmosphere then concentrated in vacuo. The residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:15) to afford N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)-6-o-tolylimidazo[1,2-b]pyridazin-8-amine (51 mg, 44%) as a yellow solid. 1H NMR (300 MHz, CD3OD): δ 8.53 (s, 1H), 7.95 (s, 1H), 7.61 (s, 1H), 7.43-7.25 (m, 5H), 6.28 (d, 1H, J=7.5 Hz), 6.02 (d, 1H, J=8.1 Hz), 4.10-4.06 (m, 1H), 3.55 (s, 1H), 3.45-3.39 (m, 1H), 3.24-3.21 (m, 1H), 2.37 (s, 3H), 2.03-1.89 (m, 3H), 1.61-1.58 (m, 1H), 0.97 (d, 3H, J=6.3 Hz). LC-MS: [M+H]+, 385, tR=1.95 min, HPLC: 99.76% at 214 nm, 100% at 254 nm, tR=4.68 min.

Provenance & Evidence