Sodium Carbonate → HCID 71534385, 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), 3-cyanophenylboronic acid (0.026 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 and ethyl acetate 3:1) to give 3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzo nitrile (0.03 g, 50%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.77 (s, 1H), 8.42 (brs, 1H), 8.26-8.21 (m, 2H), 7.90 (s, 1H), 7.75-7.36 (m, 4 h), 6.17 (d, 1H, J=7.5 Hz), 6.04 (d, 1H, J=8.1 Hz), 4.25-4.21 (m, 1H), 3.67-3.63 (m, 1H), 3.51-3.46 (m, 1H), 2.16-2.08 (m, 3H), 1.81-1.76 (m, 1H), 0.98 (d, 3H, J=6.6 Hz). LC/MS: 396 [M+H]+, tR=1.91 min. HPLC: 95.63% at 214 nm, 98.93% at 254 nm, tR=4.59 min.

Provenance & Evidence