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

Participants

Reaction Steps

BOP (253 mg, 0.571 mmol) was added to a stirred mixture of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (250 mg, 0.519 mmol), propan-2-amine (0.13 mL, 1.56 mmol) and diisopropylethylamine (0.18 mL, 1.04 mmol) in DMF (1.5 mL). The reaction was stirred at RT for 14 h then diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated. Purification on the ISCO (12 g column, 20-70% EtOAc in Hex) afforded 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (199 mg, 73%) as a white amorphous solid. MS (ESI, pos. ion) m/z: 523.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.02 (1H, d, J=8.6 Hz), 7.95 (1H, d, J=8.4 Hz), 7.86 (1H, s), 7.76-7.82 (2H, m), 7.71-7.76 (1H, m), 7.28 (2H, s), 4.54 (1H, d, J=7.6 Hz), 3.94-4.05 (1H, m), 2.37 (3H, s), 1.34 (6H, d, J=6.5 Hz).

Provenance & Evidence