Potassium Carbonate → HCID 71525433, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-N-(5-ethylpyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (329 mg, 1.21 mmol), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (221 mg, 1.81 mmol), Pd2(dba)3 (70 mg, 0.121 mmol), X-Phos (231 mg, 0.484 mmol) and K2CO3 (499 mg, 3.62 mmol) in dioxane (40 mL) and H2O (10 mL) was heated to 110° C. for 20 h under N2. The mixture was cooled and concentrated in vacuo. The residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:5) to afford N-(5-ethylpyridin-2-yl)-6-phenylimidazo[1,2-b]pyridazin-8-amine (84 mg, 22%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.69 (s, 1H), 8.37 (d, 1H, J=1.8 Hz), 8.24 (s, 1H), 8.09-8.01 (m, 3H), 7.68-7.55 (m, 5H), 7.02 (d, 1H, J=8.4 Hz), 2.75 (q, 2H, J=7.8 Hz), 1.37 (t, 3H, J=7.8 Hz). LC-MS: 316, [M+H]+, tR=1.827 min, HPLC: 99.73% at 214 nm, 99.88% at 254 nm, tR=3.262 min.

Provenance & Evidence