Dimethylformamide → 8-Cyanonaphthalene-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of 8-iodonaphthalene-2-sulfonamide (Intermediate 7, 100 mg, 0.30 mmol), ZnCN (11 μL, 0.180 mmol) and Pd(PPh3)4 (14 mg, 0.012 mmol) in DMF (1.5 mL) was purged with argon for 5 min. The reaction mixture was then heated to 125° C. in a microwave reactor for 30 min. Additional ZnCN (33 μL, 0.54 mmol) and Pd(PPh3)4 (280 mg, 0.24 mmol) were added, and the reaction mixture was heated at 125° C. for 12 h. The reaction mixture was cooled to room temperature, diluted with 10% aq. LiCl solution and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (22 mg, 30%). 1H NMR (CD3OD) δ 8.77 (d, J=0.9 Hz, 1H), 8.35 (d, J=8.4 Hz, 1H), 8.25 (d, J=8.8 Hz, 1H), 8.19 (d, J=7.3 Hz, 1H), 8.14 (d, J=1.8 Hz, 1H), 7.85-7.75 (m, 1H); MS(ESI+) m/z 250.1 (M+NH4)+.

Provenance & Evidence