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

Participants

Reaction Steps

To a solution of 2-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (21 g, 56.3 mmol) in DMF (210 mL) was added potassium tert-butoxide (12.6 g, 112.6 mol) and followed by di-tert-butyl-di-cabonate (24.5 g, 112.6 mmol). The reaction was stirred at RT for 2 h, and ice/H2O was added. The resulting precipitate was filtered and washed with H2O to give tert-butyl 3-iodo-5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (20 g, 75%). MS (ESI, pos. ion) m/z: 473.8 (M+1). 1HNMR (DMSO-d6, 300 MHz): δ 2.8 (s, 3H), 7.5 (d, 1H), 7.7 (m, 2H), 12.0 (s, 1H).

Provenance & Evidence