Pyridine → HCID 53925549, compound

Participants

Reaction Steps

At ambient temperature, to a stirred solution containing 4-[4-(9-bromo-2, 3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-2-hydroxy-benzoic acid tert-butyl ester (0.402 g, 0.602 mmol) and pyridine (0.292 mL, 3.61 mmol) in CH2Cl2 (6.02 mL) was added a solution of p-anisoyl chloride (0.208 g, 1.20 mmol) in CH2Cl2 (1.20 mL). After 18 h, the reaction was quenched with H2O (30 mL) and extracted with ether. The combined ethereal extracts were washed with sat. aq. NaHCO3 (3×), with sat. aq. CuSO4 (3×), with brine (3×), dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with 15% acetone/hexane to give 0.354 g (73%) of the title compound. 1H NMR (DMSO-d6) δ 1.33 (s, 9 H), 1.54 (s, 3 H), 2.16 (s, 6 H), 2.34 (s, 3 H), 3.90 (s, 3 H), 7.13-7.19 (m, 4 H), 7.46-7.48 (m, 2 H), 7.60-7.70 (m, 1 H), 8.08-8.13 (m, 4 H), 8.20 (d, 2 H).

Provenance & Evidence