Sodium Carbonate → HCID 86716501, compound

Participants

Reaction Steps

A mixture of tert-butyl {1-[4-(8-bromo-6-chloro-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]cyclobutyl}carbamate that was prepared in a manner analgous to that described for Intermediate Example Int-7.1 (0.15 g, 0.27 mmol), 3-pyridineboronic acid (0.040 g, 0.33 mmol, 1.2 equiv.), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (0.022 g, 0.03 mmol, 0.1 equiv.), Na2CO3 (0.086 g, 0.81 mmol, 3.0 equiv.), in dioxane (2.9 mL) and water (0.4 mL) was bubbled with Ar, then placed under an argon atmosphere and was irradiated in a microwave apparatus at 105° C. for 90 min. The reaction mixture was then added to a mixture of water (10 mL), a saturated aqueous NH4Cl solution (10 mL) and CH2Cl2 (20 mL). The resulting mixture was stirred strongly for 30 minutes. The organic phase was separated, dried (Na2SO4 anh), and concentrated under reduced pressure. The resulting material was purified using MPLC (Biotage Isolera; Snap 10 g cartridge, 100% hexane 2.0 min, gradient to 80% hexane/20% EtOAc 1.0 min, 80% hexane/20% EtOAc 3.0 min, gradient to 50% hexane/50% EtOAc 2.5 min, 50% hexane/50% EtOAc 3.5 min, gradient to 100% EtOAc 3.0 min, 100% EtOAc 4.8 min) to give tert-butyl (1-{4-[6-chloro-3-phenyl-8-(pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]phenyl}cyclobutyl)carbamate (0.046 g, 31%):

Provenance & Evidence