4-Fluorosalicylic acid → HCID 86696998, compound

Participants

Reaction Steps

To a solution of 4-fluoro-2-hydroxybenzoic acid 136 (500 mg, 3.2 mmol), (5-cyano-1-methyl-1H-pyrazol-3-yl)-N-methylmethanaminium chloride 137 (600 mg, 3.2 mmol), and HATU (1.4 g, 3.5 mmol) in DMF (21 mL) was added DIEA (2.8 mL, 16 mmol). After stirring at room temperature for 14 hours, the solution was concentrated and purified by column chromatography over silica gel eluting with heptane/ethyl acetate(0-75%) to afford compound 138 (370 mg, 40%) as a semi-solid. 1H NMR (400 MHz, 80° C., DMSO-d6) δ 10.08 (s, 1H) 7.19 (m, 1H) 6.94 (s, 1H) 6.70-6.59 (m, 2H) 4.52 (s, 2H) 3.98 (d, J=0.8 Hz, 3H) 2.86 (s, 3H). LCMS APCI m/z 298 [M+H]+.

Provenance & Evidence