Potassium Phosphate, Tribasic → HCID 89995501, 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-(fluoromethyl)pyrrolidine-1-carboxylate (22.2 mg, 0.049 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (21.56 mg, 0.097 mmol), PdCl2(dppf) CH2Cl2 Adduct (1:1) (3.99 mg, 4.85 μmol) in dioxane (0.5 ml) and 2M aq K3PO4 (0.073 ml, 0.146 mmol) in dioxane (0.5 ml) in a reaction vial was purged with N2 for 2 min. The reaction mixture was 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 column (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-(fluoromethyl)pyrrolidine-1-carboxylate (15 mg, 0.032 mmol, 65.4% yield) as a white solid. ESI-MS (Method A): m/z 473.4 ([M+H]+).

Provenance & Evidence