Water → tert-butyl 5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-(quinolin-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (80 mg, 170 μmol), 2-bromo-5-(methylthio)-1,3,4-thiadiazole (54 mg, 255 μmol), Pd(PPh3)4 (9.8 mg, 8.5 μmol) and potassium carbonate (71 mg, 510 μmol) in dioxane (1.0 mL) was added H2O (0.2 mL). The reaction was heated in a microwave at 120° C. for 70 min. The solvent was then removed and the residue was purified with silica gel chromatography to give tert-butyl 5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylate (41 mg, 51%). MS (ESI, pos. ion) m/z: 475 (M+1).

Provenance & Evidence