2,3,6-Trifluoropyridine → HCID 67426112, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 5-amino-3-cyclopropyl-1H-pyrazole-1-carboxylate (1.00 g, 4.49 mmol) in THF (15 ml) was cooled to −78° C. t-BuLi (1.7 M in THF, 4.15 mmol) was added dropwise and the resulting solution was stirred for 30 min. at −78° C. A solution of 2,3,6-trifluoropyridine (0.46 g, 3.4 mmol) in THF (5 ml) was added, and the resulting solution was stirred for 5 min at −78° C., and then the reaction was warmed to 0° C., and stirred at that temperature for 30 min. The reaction was quenched with aq. NH4Cl and extract with EtOAc (2×20 ml). The organic fractions were dried over Na2SO4, filtered, and concentrated. The resulting oil was then placed in ACN (15 ml) at 0° C., and N-trimethylsilylimidazole (0.5 ml) was added. The reaction was stirred for 20 min, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (0.10 g, 12%). MS: Calcd.: 236. Found: [M+H]+ 237.

Provenance & Evidence