HCID 22031857, compound → HCID 68328781, compound

Participants

Reaction Steps

A solution of tert-butyl 3-iodo-5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (650 mg, 1.146 mmol) and 1-methyl-4-(6-(tributylstannyl)pyridin-2-yl)piperazine (596 mg, 1.146 mmol) DMF (10 mL) was purged the Argon gas for 5 min. To the solution was added CuI (327.5 mg, 1.71 mmol), Pd(PPh3)4 (159 mg, 0.137 mmol) and again the mixture was purged the Argon gas for 5 min. The mixture was stirred at RT for 2 h, then at 90° C. for 1 h. The mixture was poured into H2O and was extracted with EtOAc. The combined organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography to give tert-butyl 3-(6-(4-methylpiperazin-1-yl)pyridin-2-yl)-5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (400 mg, 53.5%). MS (ESI, pos. ion) m/z: 555.1 (M+1); 1H-NMR (DMSO-d6, 300 MHz) δ: 9.245 (1H, s), 8.45 (1H, s), 8.35 (1H, d), 8.07 (1H, d), 7.65 (1H, m), 7.4 (1H, d), 6.85 (1H, d), 3.7-3.8 (3H, s), 3.7 (2H, brs), 2.3 (3H, s), 1.75 (9H, s), 1.2-1.3 (6H, m).

Provenance & Evidence