Trifluoroacetic acid → HCID 71150657, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-acetyl-4-[bis(tert-butoxycarbonyl)amino]-3-methoxypyridine-2-carboxylate (0.7 g, 1.649 mmol) in DCE (3.30 ml) was added Deoxo-Fluor® (1.520 ml, 8.25 mmol) and the reaction mixture was stirred at 80° C. overnight. The mixture was allowed to cool down to room temperature and TFA (2 mL) was added. The reaction mixture was stirred at room temperature (LC monitoring). After 12 h, the reaction was completed and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (ISCO, SiO2 24 g, hexane/EtOAc 100:0 to 0:100 gradient) to afford methyl 4-amino-6-(1,1-difluoroethyl)-3-methoxypicolinate (336 mg, 1.365 mmol, 83% yield) as an orange oil. ESIMS m/z 245 ([M−H]−); 1H NMR (400 MHz, CDCl3) δ 7.06 (s, 1H), 4.59 (s, 2H), 3.97 (s, 3H), 3.88 (s, 3H), 1.98 (t, J=18.7 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −89.99.

Provenance & Evidence