Nicotinic Acid → HCID 54302538, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution containing 4-[4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-2-hydroxy-benzoic acid tert-butyl ester (0.508 g, 0.863 mmol), nicotinic acid (0.108 g, 0.863 mmol), 2-chloro-1-methylpyridinium iodide (0.272 g, 1.04 mmol) and triethylamine (0.288 mL, 2.07 mmol) in CH2Cl2 (8.63 mL) was heated at 75° C. in a sealed tube for 3 days. The reaction was cooled to ambient temperature and concentrated. The crude product was purified on Biotage KP-Sil eluting with a 10 & 15% acetone/hexane step gradient to give 0.446 g (74%) of the title compound. 1H NMR (DMSO-d6) δ 1.35 (s, 9 H), 1.58 (s, 3 H), 2.18 (s, 6 H), 2.35 (s, 3 H), 7.18 (s, 2 H), 7.36-7.46 (m, 3 H), 7.68-7.72 (m, 1 H), 7.98 (d, 1 H), 8.15 (dd, 1 H), 8.22-8.26 (m, 2 H), 8.50-8.53 (m, 2 H), 8.95 (dd, 1 H), 9.30 (d, 1 H).

Provenance & Evidence