Methylamine → 3-(3-iodo-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine

Participants

Reaction Conditions

Reaction Steps

N-Methylamine (1M in THF) (5 mL) was added to a sealed tube equipped with magnetic stir bar followed by the addition of 3-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(trichloromethyl)-1,2,4-oxadiazole (250 mg, 0.43 mmol). The tube was sealed and heated at 90° C. in oil bath for 12 h. After completion of the reaction, it was cooled to RT. The mixture was treated with water and extracted with EtOAc (2×20 mL). The organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified with basic alumina column chromatography (eluent: 40% EtOAc in petroleum ether) to give 3-(3-iodo-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine (200 mg, 94.3%) as an off white solid. MS (ESI, pos. ion) m/z: 495.0 (M+1).

Provenance & Evidence