1,2-Dimethoxyethane → 6-{Difluoro-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methyl}-quinoline

Participants

Reaction Conditions

Reaction Steps

A microwave tube was charged with 6-[(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-difluoro-methyl]-quinoline (Stage 6.1, 10 mg, 0.03 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (10 mg, 0.045 mmol), tetrakis-(triphenylphosphine)palladium (1.7 mg), 2M Na2CO3 (0.054 mL) and DME (1 mL). It was heated at 150° C. under microwave irradiation for 20 min. The RM was taken up with EtOAc (2 mL) and washed with 10% Na2CO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by HPLC to afford the title compound as a brown solid (tR 1.379 min (conditions 1), MH+=376.8, 1H-NMR in DMSO-d6: 9.00 (m, 1H); 8.65 (d, 1H); 8.52 (s, 1H); 8.30 (s, 1H); 8.21 (d, 1H); 8.14 (d, 1H); 7.99 (m, 2H); 7.87 (s, 1H); 7.66 (m, 2H); 3.86 (s, 3H)).

Provenance & Evidence