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

Participants

Reaction Steps

BOP (455 mg, 1.029 mmol) was added to a stirred mixture of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (450 mg, 0.935 mmol), 2-phenylpropan-2-amine (0.442 mL, 3.27 mmol) and diisopropylethylamine (0.33 mL, 1.87 mmol) in DMF (5.0 mL). The mixture was stirred at RT for 14 h. It was treated with BOP (300 mg) and 2-phenylpropan-2-amine (0.3 mL) and heated to 65° C. for 3 h. The mixture was diluted with water and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated. Purification (eluting with 20-70% EtOAc in Hex) afforded 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine (103.6 mg, 19%) as a white amorphous solid. MS (ESI, pos. ion) m/z: 601.0 (M+1).

Provenance & Evidence