Sodium Carbonate → (S)-methyl 2-methyl-3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate

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 (124 mg, 0.38 mmol), methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (124 mg, 0.45 mmol), Pd2(dba)3 (22 mg, 0.038 mmol), X-phos (73 mg, 0.152 mmol) and Na2CO3 (121 mg, 1.14 mmol) in dioxane (10 mL) and water (1 mL) was heated to 100° C. with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=20:1) to give (S)-methyl 2-methyl-3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (72 mg, 43%) as a yellow solid. LC-MS: [M+H]+, 443.2, tR=1.880 min.

Provenance & Evidence