Sodium Carbonate → (S)-4-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid

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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 (0.08 g, 0.243 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (0.066 g, 0.268 mmol), Pd2(dba)3 (0.028 g, 0.049 mmol), X-phos (0.046 g, 0.097 mmol) and Na2CO3 (0.103 g, 0.992 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, MeOH:dichloromethane=1:10) to afford (S)-4-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (90 mg) as a yellow solid. LC-MS: [M+1]+=415, tR=1.660 min. This contained unidentified impurities and was used directly without further purification.

Provenance & Evidence