Sodium Iodide → HCID 18665173, compound

Participants

Reaction Steps

Sodium iodide (98 mg, 0.65 mmol) was added to a mixture of 3-(3-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)propyl)-5-(1,2,4-triazol-4-yl)-1H-indole (200 mg, 0.59 mmol), sodium carbonate (95 mg, 0.90 mmol) and N-(4-(2-bromoethyl)phenyl)acetamide (158 mg, 0.65 mmol) in dry 1,2-dimethoxyethane (5 ml) at room temperature under nitrogen. The mixture was then stirred and heated to reflux, protected from light, for 16 h. Upon cooling, the volatiles were removed in vacuo and the residue was partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane (x2). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 (60:8:1→50:8:1) to give the title indole (88 mg, 30%) as a foam. The bis hydrogen oxalate. 0.75 hydrate was prepared (Et2O/MeOH): mp 151-155° C. (Found: C, 57.43; H, 6.26; N, 14.35. C29H35N7O.2(C2H2O4).0.75(H2O) requires C, 57.34; H, 5.91; N, 14.18%). δ (360 MHz, d6 -DMSO) 1.94-2.02 (5H, m, includes NC(O)CH3), 2.7-3.3 (18H, m), 7.16 (2H, d, J=8.5 Hz, Ar--H), 7.30-7.36 (2H, m, Ar--H), 7.48-7.52 (3H, m, Ar--H), 7.81 (1H, s, Ar--H), 9.03 (2H, s, Triazole-H), 9.89 (1H, s, N--H), 11.17 (1H, s, N--H).

Provenance & Evidence