反应详情

温度

-25 °C

To a solution of 5-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (0.5 g, 1.12 mmol) in DMF (5 mL) at −25° C. was added NaH (0.059 g, 50% in mineral oil, 1.23 mmol) portion wise. The mixture was stirred for 5 min at −25° C. then a solution of 4-methyl benzene sulfonyl chloride (0.235 g, 1.23 mmol) in DMF (1 mL) was added at same temperature dropwise. The reaction was stirred at −25° C. for 10 min. The mixture was poured into ice cold water and a white solid precipitated out which was collected by filtration and recrystallized by triturating it with 1:3 volume of EtOH (2 mL) and CHCl3 (6 mL) to give 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (0.450 g, 0.75 mmol, 66.96%). MS (ESI, pos. ion) m/z: 601.1 (M+1); 1H-NMR (DMSO-d6) δ8.312 (s, 1H), 8.21 (s, 1H), 8.13 (s, 1H), 7.9-7.90 (m, 3H), 7.68 (s, 1H), 7.44 (d, J=9 Hz, 2H), 7.33 (d, J=9 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 4.38 (d, J=6 Hz, 2H), 3.73 (s, 3H), 2.33 (s, 3H).

1. stirringThe reaction was stirred at −25° C. for 10 min
2. additionThe mixture was poured into ice cold water
3. customa white solid precipitated out which
4. filtrationwas collected by filtration
5. customrecrystallized
6. customby triturating it with 1:3 volume of EtOH (2 mL) and CHCl3 (6 mL)