Methanol → 2-Bromo-3-[4-(2-methoxybenzyloxy)-benzenesulfonyl]-6-methylpyridine

Participants

Reaction Steps

4-(2-Bromo-6-methylpyridine-3-sulfonyl)-phenol from part E (3.22 g, 9.81 mmol), KI (1.95 g, 11.77 mmol), K2CO3 (1.63 g, 11.77 mmol), and 2-methoxybenzyl chloride (1.64 mL, 11.77 mmol) were suspended in MeCN (10 mL) and heated at reflux overnight. The mixture was cooled to rt, diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated and purified by column chromatography on silica gel (20% ethyl acetate in hexanes). Tritration with methanol afforded the desired product (3.44 g, 78% yield) as a colorless solid: mp 76–78° C.; 1H NMR (300 MHz, CDCl3) δ 8.43 (d, J=7.6 Hz, 1H), 7.82 (d, J=7.0 Hz, 2H), 7.31 (d, J=7.0 Hz, 1H), 7.25 (d, J=8.0 Hz, 2H), 7.01 (d, J=7.0, Hz, 2H), 6.92 (d, J=6.6 Hz, 1H), 6.85 (d, J=8.0 Hz, 1H), 5.10 (s, 2H), 3.80 (s, 3H), 2.53 (s, 3H); LRMS (APCI) m/z 448.0 [(M+H)+, calcd for C20H19NO4BrS, 448.0].

Provenance & Evidence