Cesium carbonate → 2-Fluoro-4-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzonitrile

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Reaction Conditions

Reaction Steps

To a vial was added 6-chloro-N-(4-methoxybenzyl)-N-phenyl imidazo[1,2-b]pyridazin-8-amine (100 mg, 0.274 mmol) from Example XXXVI(1) step (1a), 4-cyano-3-fluorophenylboronic acid (49.7 mg, 0.302 mmol), tetrakis(triphenylphosphine) palladium (17.4 mg, 0.015 mmol) and cesium carbonate (295 mg, 0.905 mmol in water (0.2 mL)) and DMF (2 mL). The solution was heated to 100° C. for 10 hours. The crude product mixture was filtered through celite, concentrated in vacuo and purified by preparative HPLC to give 2-fluoro-4-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzonitrile (30 mg, 24%). LC/MS, m/e 463 (M+1). HPLC Rt, 3.80 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min hold at 100% B 1 min, flow rate 4 mL/min.

Provenance & Evidence