Sodium Carbonate → (S)-6-(benzo[d]thiazol-6-yl)-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (0.15 g, 0.456 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole (0.119 g, 0.456 mmol), Pd2(dba)3 (0.052 g, 0.09 mmol), X-phos (0.087 g, 0.18 mmol) and Na2CO3 (0.145 g, 1.368 mmol) in dioxane (20 mL) and water (5 mL) was heated to 100° C. for 16 h in a sealed tube under N2 atmosphere then concentrated in vacuo. The residue was purified by chromatography (silica gel, 15 g, 200-300 mesh, ethyl acetate:petroleum ether=1:5) to afford (S)-6-(benzo[d]thiazol-6-yl)-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (58 mg, 51%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 9.71 (s, 1H), 9.49 (s, 1H), 8.91 (s, 1H), 8.69 (s, 1H), 8.23-8.08 (m, 3H), 7.66 (s, 1H), 7.43 (t, 1H, J=7.8 Hz), 6.74 (d, 1H, J=7.8 Hz), 6.06 (d, 1H, J=7.8 Hz), 4.26-4.23 (m, 1H), 3.59-3.55 (m, 1H), 3.44-3.40 (m, 1H), 2.08-1.98 (m, 3H), 1.69-1.66 (m, 1H), 1.09 (d, 3H, J=6.3 Hz). LC-MS: [M+H]+, 428, tR=1.997 min, HPLC: 95.07% at 214 nm, 98.34% at 254 nm, tR=4.349 min.

Provenance & Evidence