Sodium Carbonate → HCID 71526536, 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 (0.05 g, 0.15 mmol), pyridin-4-ylboronic acid (0.022 g, 0.18 mmol), Pd(dba)2 (0.02 g, 0.035 mmol), X-Phos (0.02 g, 0.042 mmol) and Na2CO3 (0.032 g, 0.3 mmol) in dioxane/H2O (20 mL/2 mL) was stirred at 95° C. for 18 h under N2 atmosphere. The solvent was removed in vacuo and the residue purified by chromatography (silica gel, petroleum ether/ethyl acetate 3:1) to give N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)-6-(pyridin-4-yl)imidazo[1,2-b]pyridazin-8-amine (0.025 g, 44%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.75-8.70 (m, 3H), 8.15 (brs, 1H), 7.93 (s, 1H), 7.86 (d, 1H, J=5.7 Hz), 7.62 (s, 1H), 7.41 (t, 1H, J=7.9 Hz), 6.22 (d, 1H, J=7.5 Hz), 6.05 (d, 1H, J=8.4 Hz), 4.26-4.22 (m, 1H), 3.68-3.63 (m, 1H), 3.49-3.46 (m, 1H), 2.16-2.04 (m, 3H), 1.77 (brs, 1H), 1.24 (t, 3H, J=6.3 Hz). LC/MS: 372 [M+H]+, 370 [M−H]−, tR=1.68 min. HPLC: 100% at 214 nm, 100% at 254 nm, tR=4.57 min.

Provenance & Evidence