Tetrahydrofuran → 5-(2-(4-Methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinic acid

Participants

Reaction Steps

Prepared using General Procedure 9: To a stirred solution of methyl 5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinate INT-14 (74 mg, 0.2 mmol) in MeOH (1 mL) and THF (4 mL) was added 2 N NaOH (1 mL). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was diluted with water (1 mL) and acidified with 1 N HCl to a pH of 2. The resulting precipitate was isolated by filtration and the filter cake was washed with water. Crude product was dried under vacuum to afford 48 mg (67%) of 5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinic acid INT-15 which was used in the next step without purification. LCMS-ESI (m/z) calculated C16H13F3N2O4: 354; found 355, tR=2.66 min (Method 1). 1H NMR (400 MHz, DMSO) δ 10.71 (s, 1H), 8.83 (d, J=2.2 Hz, 1H), 8.18 (dd, J=8.6, 2.5 Hz, 1H), 8.02 (d, J=8.6 Hz, 1H), 7.46 (d, J=8.5 Hz, 1H), 7.29-7.10 (m, 2H), 3.92 (s, 2H), 3.82 (d, J=5.3 Hz, 3H), 3.35 (s, 1H).

Provenance & Evidence