Sodium Carbonate → HCID 71526534, 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-3-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-3-yl)imidazo[1,2-b]pyridazin-8-amine (0.025 g, 44%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 9.20 (s, 1H), 8.74-8.72 (m, 2H), 8.32-8.19 (m, 2H), 7.95 (s, 1H), 7.63 (s, 1H), 7.47-7.41 (m, 2H), 6.26 (d, 1H, J=8.1 Hz), 6.07 (d, 1H, J=8.4 Hz), 4.27 (t, 1H, J=6.2 Hz), 3.69-3.64 (m, 1H), 3.50-3.47 (m, 1H), 2.17-2.05 (m, 3H), 1.79 (brs, 1H), 1.27 (d, 3H, J=6.0 Hz). LC/MS: 372 [M+H]+, tR=1.71 min. HPLC: 98.37% at 214 nm, 99.69% at 254 nm, tR=4.70 min.

Provenance & Evidence