Sodium Carbonate → HCID 71526535, 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), 4-fluorophenylboronic acid (0.025 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 6-(4-fluorophenyl)-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (0.025 g, 43%) as a yellow solid. 1H NMR (300 MHz, CD3OD): δ 8.85 (s, 1H), 8.03-7.98 (m, 3H), 7.63 (s, 1H), 7.48 (t, 1H, J=7.9 Hz), 7.30-7.24 (m, 2H), 6.34 (d, 1H, J=7.8 Hz), 6.13 (d, 1H, J=8.1 Hz), 4.30 (brs, 1H), 3.65-3.33 (m, 2H), 2.18-2.05 (m, 3H), 1.81 (brs, 1H), 1.24 (d, 3H, J=6.0 Hz) LC/MS: 389 [M+H]+, tR=2.03 min. HPLC: 95.87% at 214 nm, 99.64% at 254 nm, tR=4.79 min.

Provenance & Evidence