Cesium carbonate → N-(6-(3,3-dimethylpyrrolidin-1-yl)pyridin-2-yl)-6-phenylimidazo[1,2-b]pyridazin-8-amine

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Reaction Conditions

Reaction Steps

A mixture of 8-bromo-6-phenylimidazo[1,2-b]pyridazine (0.10 g, 0.37 mmol), 6-(3,3-dimethyl pyrrolidin-1-yl)pyridin-2-amine (0.084 g, 0.44 mmol), Pd2(dba)3 (21 mg, 0.037 mmol), BINAP (92 mg, 0.148 mmol) and Cs2CO3 (0.362 g, 1.11 mmol) in dioxane (10 mL) was heated to 100° C. for 16 h in a sealed tube under N2 atmosphere then concentrated and the residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:10) to afford N-(6-(3,3-dimethylpyrrolidin-1-yl)pyridin-2-yl)-6-phenylimidazo[1,2-b]pyridazin-8-amine (36 mg, 26%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 9.68 (s, 1H), 8.87 (s, 1H), 8.19 (d, 1H, J=1.2 Hz), 7.95-7.92 (m, 2H), 7.64 (s, 1H), 7.53-7.40 (m, 4 h), 6.72 (d, 1H, J=7.8 Hz), 6.02 (d, 1H, J=8.1 Hz), 3.51 (t, 1H, J=6.9 Hz). 3.30 (s, 2H), 1.81 (t, 2H, J=6.9 Hz), 1.13 (s, 6H). LC-MS: [M+H]+, 385, tR=2.099 min, HPLC: 96.88% at 214 nm, 97.82% at 254 nm, tR=8.077 min.

Provenance & Evidence