Triethylamine → HCID 67479985, compound

Participants

Reaction Steps

To a solution of tert-butyl N-(5-bromo-3-ethynyl-2-pyridyl)-N-tert-butoxycarbonyl-carbamate (423 mg, 1.065 mmol) and N-hydroxy-4-methyl-benzimidoyl chloride (212.5 mg, 1.065 mmol) [Bioorganic & Medicinal Chemistry, 17(13), 4773-4785; 2009] in THF (10 mL) at ambient temperature was added Et3N (129.3 mg, 178.1 μL, 1.278 mmol) dropwise. The mixture was stirred at ambient temperature for 16 hours then at 65° C. for 2 hours. The mixture was concentrated in vacuo and the residue redissolved in DCM and washed with saturated aqueous NaHCO3 (×2) and brine (×1). The organic fraction was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 40 g column, eluting with 0 to 20% EtOAc/Petroleum Ether, loaded in DCM) to give the sub-title product as a white solid (472 mg, 84% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.28 (s, 18H), 2.39 (s, 3H), 7.39 (d, 2H), 7.60 (s, 1H), 7.68 (d, 2H), 8.73 (d, 1H) and 8.82 (d, 1H) ppm; MS (ES+) 532.0.

Provenance & Evidence