2-Isopropoxy-6-(tributylstannyl)pyridine → 5-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine

온도

90 °C

A solution of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.8 g, 1.29 mmol) and 2-isopropoxy-6-(tributylstannyl)pyridine (0.83 g, 1.95 mmol) in DMF (8 mL) was bubbled with Argon for 15 min. To the above mixture was added CuI (0.124 g, 0.65 mmol) and Pd(PPh3)4 (0.15 g, 0.13 mmol) and argon gas was purged for another 15 min. The reaction was heated at 90° C. for 1 h. The mixture was treated with ice cold water (20 mL) to obtain off white precipitate. The precipitate was filtered, washed with H2O (20 mL) and dried. The solid was purified by basic alumina chromatography (eluent: 20% EtOAc in petroleum ether) to give 5-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.35 g, 43%) as a white solid. MS (ESI, pos. ion) m/z: 625.2 (M+1); 1H-NMR (400 MHz, CDCl3): δ 9.02 (d, J=1.2 Hz, 1H), 8.10-8.08 (m, 2H), 7.96 (dd, J=8.8, 2.0 Hz, 1H), 7.83 (d, J=8.4 Hz, 2H), 7.64 (t, J=8.0 Hz, 1H), 7.34-7.24 (m, 2H) 4.62 (d, J=5.6 Hz, 2H), 3.80 (s, 3H), 2.35 (s, 3H), 1.46 (d, J=5.6 Hz, 6H).

1. customwas purged for another 15 min
2. additionThe mixture was treated with ice cold water (20 mL)
3. customto obtain off white precipitate
4. filtrationThe precipitate was filtered
5. washwashed with H2O (20 mL)
6. customdried
7. customThe solid was purified by basic alumina chromatography (eluent: 20% EtOAc in petroleum ether)

ORD 기록

ord-64b58d684776456f85556c940f3c4a00

출처 데이터셋

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09321756B2