Hexachloroethane → HCID 86656723, compound

Participants

Reaction Steps

To a suspension of 8-(3,5-bis(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (prepared in analogy to example 66a-c) (80 mg, 231 μmol) and hexachloroethane (65.6 mg, 277 μmol) under argon in dry THF (4 mL) was added triethylamine (70.1 mg, 96.6 μL, 693 mmol) followed by trimethylphosphine (1 M in THF, 277 μL, 277 μmol). The reaction mixture was stirred at room temperature for 0.5 hours, then tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate (example 238b, 60.2 mg, 277 μmol) was added and the mixture heated to 150° C. for 30 minutes in the microwave. A solution of decaborane (28.2 mg, 30.0 μL, 231 μmol) in dry methanol (1 mL) was added to the reaction mixture and stirred at room temperature for 3 hours. Aqueous NaHCO3 solution was added to the reaction mixture, the aqueous phase was extracted with CH2Cl2, the organic layers were combined, dried over Na2SO4, filtered and the solvents evaporated. The residue was purified by flash chromatography (silica gel, 50 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane). The title compound was obtained as off-white foam (107 mg, 85%) as a mixture of cis- and trans-isomers.

Provenance & Evidence