Nitrogen → HCID 89995499, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (3S,4S)-tert-butyl 3-((2-bromo-7-carbamoylimidazo[1,2-b]pyridazin-8-yl)amino)-4-ethylpyrrolidine-1-carboxylate (200 mg, 0.441 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (147 mg, 0.662 mmol) in 2M aq K3PO4 (0.662 ml, 1.324 mmol) and dioxane (2 ml) was purged with N2 for 2 min, followed by addition of PdCl2(dppf) CH2Cl2 Adduct (1:1) (36.3 mg, 0.044 mmol). The reaction mixture was purged with nitrogen for 2 min, sealed and heated at 100° C. for 120 min. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with brine, filtered through CELITE®, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (ISCO 12 g column, 20-80% EtOAc/hexane over 15 min) to afford (3S,4S)-tert-butyl 3-((7-carbamoyl-2-(1-ethyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-8-yl)amino)-4-ethylpyrrolidine-1-carboxylate as an off-white solid.

Provenance & Evidence