Ethanol → Ethyl 7-sulfamoyl-1-naphthoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-iodonaphthalene-2-sulfonamide (Intermediate 7, 200 mg, 0.60 mmol) in dioxane (2.0 mL) in a microwave tube was added EtOH (400 μL, 6.00 mmol), molybdenum hexacarbonyl (81 μL, 0.60 mmol) and Pd(OAc)2 (17 mg, 0.075 mmol). DBU (270 μL, 1.80 mmol) was then added, and the sealed tube was placed in the microwave and heated at 100° C. for 20 min. The reaction mixture was cooled to room temperature and quenched with 10% aq. LiCl solution. The solution was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified using preparative HPLC to give the title compound (22 mg, 13%). 1H NMR (CD3OD) δ 9.54 (d, J=0.9 Hz, 1H), 8.31 (dd, J=7.4, 1.2 Hz, 1H), 8.20 (d, J=8.4 Hz, 1H), 8.13 (d, J=8.8 Hz, 1H), 8.00 (dd, J=8.7, 1.9 Hz, 1H), 7.72 (dd, J=8.2, 7.4 Hz, 1H), 4.50 (q, J=7.0 Hz, 2H), 1.48 (t, J=7.2 Hz, 3H); MS (ESI−) m/z 278.4 (M−H)−.

Provenance & Evidence