反应详情

温度

90 °C

A solution of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.78 g, 1.26 mmol) and N-isopropyl-6-(tributylstannyl)pyrazin-2-amine ((0.65 g, 1.52 mmol) in DMF (8 mL) was purged with argon for 15 min. To the above mixture, CuI (0.289 g, 1.52 mmol) and Pd(PPh3)4 (0.146 g, 0.126 mmol) was added and argon gas was purged for another 15 min. The reaction was heated at 90° C. for 1 h, then cooled to RT. The mixture was treated with ice cold H2O to obtain off brown precipitate. The precipitate was filtered and washed with H2O and dried. The crude was purified by neutral alumina column chromatography (eluent: 20% EtOAc in petroleum ether) to give 5-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.5 g, 63.5%) as an off brown solid. MS (ESI, pos. ion) m/z: 626.2 (M+1); 1H-NMR (300 MHz, DMSO-d6): δ 9.02 (brs, 1H), 8.70 (s, 1H), 8.18-8.16 (m, 1H), 7.99 (m, 2H), 7.65-7.75 (m, 3H), 7.44-7.40 (m, 3H), 7.30-7.28 (m, 2H), 1.70-7.68 (m, 1H), 6.88 (m, 1H), 4.42 (m, 2H), 3.71 (s, 3H), 2.31 (s, 3H), 1.56 (m, 6H).

1. customargon gas was purged for another 15 min
2. temperaturecooled to RT
3. additionThe mixture was treated with ice cold H2O
4. customto obtain off brown precipitate
5. filtrationThe precipitate was filtered
6. washwashed with H2O
7. customdried
8. customThe crude was purified by neutral alumina column chromatography (eluent: 20% EtOAc in petroleum ether)