Potassium Phosphate, Tribasic → 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

To the solution of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (1.0 g, 1.66 mmol) and 6-chloropyridin-2-ylboronic acid (0.392 g, 2.49 mmol) in DMF (10 mL) was added K3PO4 (0.704 g, 3.32 mmol) and this solution was purged under N2 for 15 min. Then Pd(PPh3)4 (0.176 g, 0.152 mmol) was added and the reaction was heated at 85° C. for 5 h. The solution was poured in ice cold water (50 mL) and extracted with EtOAc. The combined organic layers were washed with H2O, dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 15% EtOAc in Hex) to give 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (0.52 g, 53.3%) as a brown solid. MS (ESI, pos. ion) m/z: 586 (M+1); 1H NMR (DMSO-d6, 300 MHz): δ ppm 8.94 (s, 1H), 8.79 (s, 1H), 8.16-8.14 (m, 2H), 8.03-7.97 (m, 4H), 7.67-7.55 (m, 1H), 7.49-7.42 (m, 3H), 7.34 (d, J=8.4 Hz, 2H), 6.9 (d, J=8.1 Hz, 2H), 4.38 (s, 2H), 3.72 (s, 3H), 2.32 (s, 3H).

Provenance & Evidence