Potassium Carbonate → HCID 68349400, compound

Participants

Reaction Conditions

Reaction Steps

Pd2 dba3 (0.850 mg, 0.928 mmol) and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (1.770 mg, 3.71 mmol) were added to a degassed (nitrogen bubbled through for ca. 10 min) solution of (+/−)-6-bromo-4-(1-cyclopropylethylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 9, 20 mg, 0.062 mmol), 6-methyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione (21.72 mg, 0.093 mmol), potassium carbonate (42.8 mg, 0.309 mmol) and copper (II) acetate (5.62 mg, 0.031 mmol). The vial was sealed (screw-cap) and immersed in an oil bath pre-heated to 100° C. The reaction was allowed to stir at this temperature for 2 hrs. After cooling to rt, the mixture was filtered and purified by direct injection onto a preparative HPLC (condition A) to give the title compound (7.63 mg, 0.023 mmol, 36.4% yield). HPLC (condition I): retention time=5.08 minutes. LC/MS (M+H)+=m/z 322.2. 1H NMR (500 MHz, MeOD) δ ppm 8.69 (1 H, d, J=4.99 Hz), 8.40-8.49 (1 H, m), 8.32-8.40 (1 H, m), 8.28 (1 H, s), 7.76 (1 H, td, J=6.59, 1.25 Hz), 7.68 (1 H, d, J=1.94 Hz), 7.52 (1 H, d, J=1.94 Hz), 4.12 (1 H, quin, J=6.45 Hz), 1.52 (2 H, d, J=6.38 Hz), 1.14-1.29 (1 H, m), 0.58-0.75 (1 H, m), 0.35-0.51 (1 H, m).

Provenance & Evidence