Sodium ethanethiolate → 8-(Ethylthio)naphthalene-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of 8-iodonaphthalene-2-sulfonamide (Intermediate 7, 100 mg, 0.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (12 mg, 0.015 mmol) and sodium ethanethiolate (50 mg, 0.60 mmol) in DMF (2 mL) was purged with argon. The reaction mixture was heated to 50° C. for 12 h. Additional sodium ethanethiolate (25 mg, 0.30 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (240 mg, 0.30 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 (24 mg, 30%). 1H NMR (CD3OD) δ 9.02-8.98 (m, 1H), 8.08-8.03 (m, 1H), 8.00-7.95 (m, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.73 (dd, J=7.4, 1.0 Hz, 1H), 7.64-7.57 (m, 1H), 3.09 (q, J=7.3 Hz, 2H), 1.34 (t, J=7.4 Hz, 3H); MS(ESI−) m/z 266.2 (M−H)−.

Provenance & Evidence