Triphenylarsine → HCID 10192938, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[2-(cyclopropylamino)-4-pyrimidinyl]pyrazolo[1,5-b]pyridazin-6-yl trifluoromethanesulfonate (100 mg, 0.25 mmol) in DMF (3 mL) was added Pd2(dba)3 (12 mg, 0.0125 mmol), LiCl (32 mg, 0.75 mmol), AsPh3 (31 mg, 0.10 mmol), and vinyl-tributylstannane (120 mg, 0.375 mmol). The reaction mixture was heated at an oil bath temperature of 60° C. for about 4 hours. The mixture was cooled to RT and water (20 mL) was added. The aqueous layer was washed with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo and purified by silica-gel column chromatography (gradient, 10-80% EtOAc in hexanes) to give the title compound as an off-white solid (26 mg, 37%). 1H-NMR (300 MHz, CDCl3) δ 9.05 (d, 1H, J=9.3 Hz), 8.44 (s, 1H), 8.30 (d, 1H, J=5.3 Hz), 7.40 (d, 1H, J=9.4 Hz), 6.92 (m, 2H), 6.22 (d, 1H, J=17.7 Hz), 5.75 (d, 1H, J=11.2 Hz), 5.48 (bs, 1H), 2.86 (m, 1H), 0.90 (m, 2H), 0.66 (m, 2H); MS (ESI) (M+H)+ 279.

Provenance & Evidence