Potassium Phosphate, Tribasic → HCID 68292325, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-methyl 3-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-2,2-dimethylbutanoate (170 mg, 0.444 mmol) and (6-methoxypyridin-3-yl) boronic acid (102 mg, 0.665 mmol) were taken in 1,4-dioxane (5 mL) in a sealed tube. To this mixture were added 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (21.15 mg, 0.044 mmol) and palladium (II) acetate (4.98 mg, 0.022 mmol) followed by K3PO4 (2M solution) (0.554 mL, 1.109 mmol). The reaction mixture was degassed and heated to 135° C. for 1 h. After completion of the reaction, the reaction mixture was cooled, quenched with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (60 mL), dried over anhyd. sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product as a brown liquid. The crude product was purified by flash chromatography over silica gel and eluted using 40% ethyl acetate in petroleum ether to give the title compound (125 mg, 0.293 mmol, 66.2% yield) as an off white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.24-1.25 (d, J=1.6 Hz, 6H), 1.28-1.3 (d, J=6.8 Hz, 3H), 3.57 (s, 3H), 3.89 (s, 3H), 4.65-4.69 (m, 1H), 6.87-6.89 (d, J=8.4 Hz, 1H), 7.28-7.29 (d, J=1.6 Hz, 1H), 8.12-8.15 (dd, J=2.4 Hz, J=2.8 Hz, 1H), 8.205-8.209 (d, J=1.6 Hz, 2H), 8.65-8.66 (d, J=2.4 Hz, 1H), 10.91-10.94 (d, J=10 Hz, 1H). [α]24.8=8.0 (c=0.1, MeOH).

Provenance & Evidence