Potassium Phosphate, Tribasic → HCID 86676943, compound

Participants

Reaction Steps

A microwave vial was charged with a mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (1.1 g, 4.73 mmol), 4-methylpyridin-3-ylboronic acid (0.648 g, 4.73 mmol), tetrakis(triphenylphosphine)palladium(0) (0.547 g, 0.473 mmol), dioxane (14 mL), and K3PO4 (7.10 mL, 14.20 mmol) (2.0 M water solution) was stirred at room temperature for 5 min. under nitrogen. The resulting mixture was heated to 100° C. for 8 h in microwave. The reaction mixture was cooled to room temperature, quenched with water, and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by BIOTAGE® (20-80% EtOAc/CH2Cl2, 1.5 L, then 20%-65% B/CH2Cl2, 0.9 L; B: 10% MeOH/CH2Cl2) to give 400 mg (34%) product. 1H NMR (400 MHz, CD3OD) δ ppm 9.00 (1H, s), 8.80 (1H, d, J=5.79 Hz), 8.38 (1H, d, J=1.51 Hz), 8.04 (1H, d, J=6.04 Hz), 7.96 (1H, d, J=1.51 Hz), 7.86 (1H, s), 2.73 (3H, s); LC/MS: Rt=0.98 min. LC/MS (Condition A): 245.11/247.08.

Provenance & Evidence