2,2,2-Trifluoroethylhydrazine → 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-N'-(2,2,2-trifluoroethyl)-3-pyridinecarboxylic acid hydrazide

Beteiligte Stoffe

Reaktionsschritte

5-(4-Chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (1000 mg, 3.02 mmol; CAN 1018782-82-5) and (2,2,2-trifluoroethyl)hydrazine (380 mg, 3.33 mmol; CAN 5042-30-8) were combined with DMF (10 mL) to give a colorless solution. TBTU (1.06 g, 3.32 mmol) and DIPEA (1.56 g, 2.05 mL, 12.1 mmol) were added. The reaction mixture was stirred for 15 h at room temperature. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layers were combined and washed with water (1×50 mL) and brine (1×50 mL). The organic layers were dried with MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 50 g, 0% to 50% EtOAc in hexane) to give the title compound (0.35 g, 27%) as white solid; LC-MS (UV peak area/ESI) 100%, 426.0451 (M−H)−.

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