Triethylamine → HCID 67480060, compound

Participants

Reaction Steps

NCS (62.52 mg, 0.4682 mmol) was added to a solution tert-butyl 3-fluoro-4-((hydroxyimino)methyl)benzyl(methyl)carbamate [prepared in an analogous manner to that described in Bioorganic & Medicinal Chemistry, 17(13), 4773-4785; 2009] (132.2 mg, 0.4682 mmol) in DMF (930.0 μL) and the mixture heated at 55° C. for 15 minutes. The reaction mixture was allowed to cool to room temperature, and tert-butyl N-(5-bromo-3-ethynyl-2-pyridyl)-N-tert-butoxycarbonyl-carbamate (186 mg, 0.4682 mmol) and Et3N (56.85 mg, 78.31 μL, 0.5618 mmol) were added. The mixture was stirred at ambient temperature for 45 minutes followed by heating to 65° C. for 1 hour. The mixture was cooled to ambient temperature and diluted with ethyl acetate (5 mL) and water (5 mL) and the layers separated. The aqueous layer was extracted further with ethyl acetate (2×5 mL) and the combined organic extracts washed with water (3×10 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, loaded in DCM) to give the impure sub-title product as a tacky yellow oil. This was used in the next step without further purification.

Provenance & Evidence