Ethanol → Ethyl 7-sulfamoyl-2-naphthoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-iodonaphthalene-2-sulfonamide (Intermediate 11, 70 mg, 0.21 mmol) in DMF (2.0 mL) and EtOH (2.0 mL, 34.2 mmol) was added bis(triphenylphosphine)palladium chloride (74 mg, 0.11 mmol). After purging the solution with nitrogen, the reaction flask was evacuated and refilled with CO. The reaction mixture was heated to 70° C. for 3 h. Pd(OAc)2 (47 mg, 0.21 mmol) was then added, and the reaction flask was evacuated and refilled with CO. After stirring under CO overnight at 70° C., the reaction mixture was cooled to room temperature, taken up in a biphasic mixture of EtOAc and water, and filtered. The layers were separated and the aqueous layer was extracted with EtOAc (3×). The combined organic fractions were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (20 mg, 34%) as a white solid. 1H NMR (MeOD) δ 8.82 (s, 1H), 8.63 (d, J=1.3 Hz, 1H), 8.22 (d, J=8.8 Hz, 1H), 8.17-8.12 (m, 2H), 8.02 (dd, J=8.6, 2.0 Hz, 1H), 7.52 (s, 2H), 4.40 (q, J=7.0 Hz, 2H), 1.38 (t, J=7.2 Hz, 3H); MS(ESI−) m/z 278.3 (M−H)−.

Provenance & Evidence