Reaction Steps
Under N2, the product of Example 1A (329 mg, 1 mmol), 5-indolylboronic acid (Frontier, 193 mg, 1.2 mmol), Pd2(dba)3 (Aldrich, 24 mg, 0.025 mmol), (tBu3P)2Pd (26 mg, 0.05 mmol), K2CO3 (276 mg, 2 mmol) and KF (80 mg, 1.4 mmol) in THF (8 mL) was stirred at 60° C. overnight. The reaction was monitored with TLC. After the reaction was complete, it was diluted with EtOAc (30 mL) and washed with brine (2×5 mL). The organic solution was concentrated under reduced pressure and the title product was purified by preparative HPLC (Gilson, column, Symmetry® C-8 7 μm, 40×100 mm. Eluting Solvent, MeCN/H2O (with 0.2% v. TFA) (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (80 mg, yield, 25%). 1H NMR (300 MHz, CD3OD) δ 1.44–1.58 (m, 1H), 1.62–1.90 (m, 2H), 2.01–2.15 (m, 1H), 2.16–2.24 (m, 1H), 2.74–3.04 (m, 5H), 3.27–3.40 (m, 1H), 4.51–4.59 (m, 1H), 6.46 (dd, J=3.4, 1.1 Hz, 1H), 6.95 (dt, J=8.8, 2.6 Hz, 2H), 7.22 (d, J=3.1 Hz, 1H), 7.31 (dd, J=8.5, 2.0 Hz, 1H), 7.40 (dt, J=8.5, 1.0 Hz, 1H), 7.54 (dt, J=9.2, 2.6 Hz, 2H), 7.71 (dd, J=1.7, 0.7 Hz, 1H) ppm. MS (DCl/NH3): m/z 319 (M+H)+.
