Potassium Phosphate, Tribasic → HCID 68291675, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-4-(ethylthio)pyrrolo[1,2-b]pyridazine-3-carboxamide (1.2 g, 4.00 mmol), phenylboronic acid (0.731 g, 6.00 mmol), palladium (II) acetate (0.090 g, 0.400 mmol), 2M potassium phosphate, tribasic (7.60 mL, 15.19 mmol) and 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbyphenyl (0.381 g, 0.800 mmol) in dioxane (volume: 30 mL) was heated to 125° C. in a pressure vessel, behind a blast shield for 4 hr. Additional phenylboronic acid (0.366 g, 3.00 mmol), palladium (II) acetate (0.045 g, 0.200 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (0.191 g, 0.400 mmol) and 2M potassium phosphate, tribasic (7.60 mL, 15.19 mmol) were added and heating was continued for 1 hr. The reaction mixture was partitioned between EtOAc (250 ml) and water (250 ml). The organic layer was washed with brine (100 ml), dried (MgSO4) and concentrated to a yellow solid that was triturated with ethyl ether. Filtration, washing with ethyl ether/hexane, 1:1 and drying afforded the title compound (0.91 g, 3.06 mmol, 77% yield) as a yellow solid that was used in the next step without further purification. 1H NMR (400 MHz, MeOD) δ ppm 1.28 (t, J=7.4 Hz, 3 H) 3.19 (q, J=7.5 Hz, 2 H) 7.23 (d, J=1.8 Hz, 1 H) 7.28 (d, J=7.5 Hz, 1 H) 7.40 (t, J=7.7 Hz, 2 H) 7.74 (d, J=7.3 Hz, 2 H) 8.16 (s, 1 H) 8.21 (d, J=1.8 Hz, 1 H). LCMS (M+H)=298.07.

Provenance & Evidence