Potassium Carbonate → 2-(1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-5-(methylthio)-1,3,4-thiadiazole (18.5 g, 87 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (21 g, 86 mmol) in p-dioxane (5 mL)/H2O (5 mL) was added Pd(PPh3)4 (15.1 g, 13 mmol) followed by K2CO3 (48.2 g, 349 mmol). The reaction was heated under argon atmosphere at 110° C. for 4 h, then cooled to RT. The mixture was diluted with EtOAc and H2O, and the two layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The crude material was recrystallized in EtOH to give 2-(1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (10 g, 50%) as an off-white solid. MS (ESI, pos. ion) m/z: 247.8 (M+1). 1H-NMR (DMSO-d6, 300 MHz): 2.8 (s, 3H), 6.6 (d, 1H), 7.5 (t, 1H), 7.55 (dd, 1H), 8.1 (s, 1H), 11.5 (s, 1H).

Provenance & Evidence