Sodium Carbonate → [2-(2-Hydroxymethyl-4-methoxy-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Participants

Reaction Steps

Dissolve trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester (300 mg, 0.56 mmol), 5-methoxy-3H-benzo[c][1,2]oxaborol-1-ol(275 mg, 1.7 mmol) and 2M sodium carbonate (0.5 mL, 13 mmol) in dimethoxyethane (5.0 mL). Degas the solution with nitrogen for 15 min. Add tetrakis(triphenylphosphine)palladium (130 mg, 0.11 mmol) and heat at 60° C. for 2 hours. Cool reaction to room temperature and purify on a SCX column to yield 294 mg (100%) of the title compound as a pale yellow foam. 1H NMR (CDCl3) 7.84 (d, J=8.4 Hz, 1H), 7.67 (m, 2H), 7.48 (m, 1H), 7.39 (m, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.23 (d, J=2.5 Hz, 1H), 7.07 (d, J=8.8 Hz, 1H), 7.03 (bs, 1H), 6.82 (m, 2H), 6.57 (m, 1H), 4.44 (m, 1H), 4.28 (bs, 1H), 4.15 (bs, 2H), 3.94 (s, 3H) 3.78 (s, 3H), 2.81 (bs, 2H), 2.52 (bs, 4H) 1.61 (m, 4H), 1.44 (bs, 2H).

Provenance & Evidence