Reaction Steps
A microwave vial equipped with a magnetic stirrer was charged with 109e (300 mg, 0.75 mmol), 4-fluoro-2-(1-oxo-3,4,6,7,8,9-Hexahydropyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 101l (545 mg, 1.13 mmol), potassium carbonate (414 mg, 3.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (68 mg, 0.075 mmol), and tricyclohexylphosphine (210 mg, 0.75 mmol). After bubbling nitrogen through the suspension for 5 minutes, the reaction was heated at 110° C. for overnight. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 109 as a white solid (71 mg, 14%). LCMS: [M+H]+ 677.3. 1H NMR (500 MHz, DMSO) δ 8.64 (s, 1H), 8.23 (d, J=1.0, 1H), 8.18 (s, 1H), 7.88 (d, J=2.5, 1H), 7.38-7.39 (m, 1H), 7.33-7.35 (m, 1H), 7.24 (d, J=9.0, 1H), 7.18-7.19 (m, 2H), 6.52 (s, 1H), 4.85 (bs, 1H), 4.56 (t, J=6.0, 2H), 4.46 (t, J=6.0, 2H), 4.29 (s, 2H), 4.16-4.18 (m, 3H), 3.93-3.94 (m, 1H), 3.84 (s, 3H), 3.44-3.45 (m, 1H), 3.07 (t, J=4.0, 4H), 2.61-2.62 (m, 2H), 2.47 (t, J=6.0, 2H), 2.39 (t, J=4.0, 4H), 1.79-1.80 (m, 2H), 1.70-1.71 (m, 2H)
