Sodium Carbonate → HCID 71526618, compound

Participants

Reaction Steps

To a solution of 6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (60 mg, 0.183 mmol) and 4-tert-butylphenylboronic acid (49 mg, 0.274 mmol) in dioxane/H2O (10 mL/1 mL) was added Na2CO3 (39 mg, 0.366 mmol) followed by Pd(dba)2 (21 mg) and X-Phos (9 mg) under nitrogen with stirring. The mixture was refluxed for 15 h under nitrogen. After cooling, the solvent was concentrated in vacuo. The residue was purified by chromatography (silica, dichloromethane:MeOH=100:1) to give 6-(4-tert-butylphenyl)-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyri-dazin-8-amine (30 mg, 38%) as a solid. 1H NMR (300 MHz, CDCl3): δ 8.70 (s, 1H), 8.30 (brs, 1H), 7.90 (d, 1H, J=7.5 Hz), 7.60 (s, 1H), 7.51-7.38 (m, 4 h), 6.31 (d, 1H, J=7.2 Hz), 6.03 (d, 1H, J=8.1 Hz), 4.24 (brs, 1H), 3.66 (brs, 1H), 3.49-3.47 (m, 1H), 2.15-2.09 (m, 3H), 1.75 (brs, 1H), 1.38 (s, 9H), 1.23 (d, 3H, J=6.3 Hz). LC/MS: 427 [M+H]+, tR=2.51 min. HPLC: 95.63% at 214 nm, 99.19% at 254 nm, tR=99.79% min.

Provenance & Evidence