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

Participants

Reaction Steps

To a mixture of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (585 mg, 1.216 mmol), methylamine (1.82 mL of 2 M in THF, 3.65 mmol) and diisopropylethylamine (0.42 mL, 2.43 mmol) in DMF (1.5 mL) was added 1H-benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (V) (591 mg, 1.33 mmol). The reaction was stirred at RT for 18 h, then diluted with H2O (5 mL) and extracted with EtOAc (2×15 mL). The combined organic solution was washed with brine, dried over MgSO4, and concentrated. The residue was suspended in 5 mL of EtOAc, and filtered to 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-methyl-1,3,4-oxadiazol-2-amine (507 mg, 84%) as an off white crystalline solid. MS (ESI, pos. ion) m/z: 495.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.21 (1H, s), 8.13 (1H, d, J=8.8 Hz), 7.98 (2H, d, J=8.4 Hz), 7.91 (1H, m), 7.71 (1H, m), 7.70 (1H, m), 7.44 (2H, d, J=8.0 Hz), 2.88 (3H, d, J=4.9 Hz), 2.35 (3H, s).

Provenance & Evidence