Potassium Carbonate → 5-(3-(6-(4-fluorophenyl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Steps

To a solution of 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (500 mg, 0.853 mmol) and 4-fluorophenylboronic acid (143.5 mg, 1.02 mmol) in 1,4-dioxane/H2O (3:1, 15 mL), was added K2CO3 (235.5 mg, 1.71 mmol) and Pd(PPh3)4 (49 mg, 0.0427 mmol). The reaction was heated at reflux for 24 h then quenched with H2O and extracted with EtOAc. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 50% EtOAc in Hex) to give 5-(3-(6-(4-fluorophenyl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (200 mg, 36.5%). MS (ESI, pos. ion) m/z: 647.1 (M+1); 1H-NMR (400 MHz DMSO-d6): δ 12.11 (s, 1H), 9.18 (s, 1H), 9.08-8.98 (m, 2H), 8.52 (d, J=2.8 Hz, 1H), 8.36-8.33 (m, 2H), 8.14-8.03 (m, 1H), 7.74 (d, J=8 Hz, 1H), 7.65-7.55 (m, 2H), 7.46-7.7.28 (m, 4H), 6.92-6.88 (m, 2H), 4.41 (m, 2H), 3.73 (s, 3H), 2.24 (s, 3H).

Provenance & Evidence