3-Bromo-4-methylpyridine → N-(4-(4-Methylpyridin-3-yl)-3-(trifluoromethyl)phenyl)methanesulfonamide

Participants

Reaction Steps

The compound of Example 240 was prepared by the procedure described for the preparation of Intermediate 1C using Intermediate 52 and 3-bromo-4-methylpyridine. The crude material was purified by reverse phase preparative HPLC using a PHENOMENEX® Luna 30×100 mm column with a linear gradient of Solvent A (10% methanol/90% water with 0.1% TFA) and Solvent B (90% methanol/10% water with 0.1% TFA) over 12 min with peak detection at 254 nM. Collected fractions were applied to a 1 g Waters OASIS® MCX cation exchange cartridge, which was washed with methanol and 2 M ammonia in methanol, to provide the title compound (43 mg, 58%) as a solid: HPLC Ret timed: 1.21 min. MS: m/z=331 [M+H]+; 1H NMR (400 MHz, CD3OD) δ ppm 8.42 (1 H, d, J=5.0 Hz), 8.24 (1 H, s), 7.70 (1 H, s), 7.60 (1 H, d, J=8.3 Hz), 7.24-7.49 (2 H, m), 3.09 (3 H, s), 2.12 (3 H, s); 19F NMR (CD3OD) δ ppm 60.8.

Provenance & Evidence