Potassium Carbonate → HCID 68291720, compound

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a mixture of 6-bromo-4-(propylamino) pyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 8, 20 mg, 0.067 mmol), phenylboronic acid (24.62 mg, 0.202 mmol), tetrakis(triphenylphosphine) palladium(0) (7.78 mg, 6.73 μmol) and potassium carbonate, 2M (0.135 mL, 0.269 mmol) in dimethoxyethane (0.6 mL) for ˜1 minute. The reaction mixture was then heated to 90-95° C. for 2 hr. The reaction mixture was partitioned between EtOAc (20 ml) and water (20 ml). The organic layer was washed with brine (20 ml), dried (MgSO4) and concentrated to a brown residue that was dissolved in MeOH and was subjected to preparative HPLC (Phenomenex 30×100 mm S-5 column; eluting with 45-90% aqueous MeOH+0.1% TFA over an 12 minute gradient, flow rate=1 mL/min, 220 wavelength detection). The product containing fraction was concentrated to afford the title compound (16 mg, 0.054 mmol, 80% yield) as a tan solid. HPLC (condition M): retention time=2.93 min.; LCMS (ES+) m/z: 295.14 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.12 (t, J=7.3 Hz, 3 H), 1.77-1.87 (m, 2 H), 3.83 (t, J=6.5 Hz, 2 H), 7.20-7.31 (m, 2 H), 7.32-7.44 (m, 2 H), 7.66 (d, J=7.5 Hz, 2 H), 7.91 (s, 1 H), 8.09 (s, 1 H).

Provenance & Evidence