2-Methylpyridine → HCID 58920622, compound

Participants

Reaction Conditions

Reaction Steps

2-Methyl pyridine (48 μL, 0.49 mmol) in THF (90 μL) was cooled at −78° C. for 10 min, followed by the addition of n-BuLi (246 μL, 0.49 mmol, 2M solution in cyclohexane). The reaction turned into maroon and was stirred at −78° C. for 40 min. (R,Z)-N-((5-chloropyridin-2-yl)(3-fluoro-5-(trifluoromethyl)phenyl)methylene)-2-methylpropane-2-sulfinamide (100 mg, 0.25 mmol) in THF (1 mL) was added and the dark green colored reaction mixture was stirred at −78° C. for another 2 h. Quenched with H2O (10 mL), the reaction mixture was extracted by EtOAc (2×15 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by preparative HPLC YMC ODS S5 28×100 mm Ballistic column 40-100% MeOH (90% in water, 0.1% TFA) gradient over 12 min with flow rate 40 mL/min and UV detection at 220 nm. (S)-N-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-(pyridin-2-yl)ethyl)-2-methylpropane-2-sulfinamide at a retention time of 9.66 min and was isolated as a clear oil (48 mg, yield 38%) LCMS: 1.76 min [M+1] 500.2 (2 min gradient, MeOH/H2O 0.1% TFA); HPLC: 3.72 min (4 min gradient, MeOH/H2O 0.2% PPA); Purity 100%; NMR: 400 MHz 1H (CDCl3) 8.45 ppm, 1 H, d, J=2.64 Hz; 8.28 ppm, 1 H, d, J=4.39 Hz; 7.93 ppm, 1 H, s; 7.68 ppm, 1 H, d, J=8.79 Hz; 7.48 ppm, 1 H, dd, J=8.57, 2.42 Hz; 7.35 ppm, 1 H, t, J=6.81 Hz; 7.31 ppm, 1 H, s; 7.10 ppm, 1 H, d, J=7.91 Hz; 6.97 ppm, 2 H, m; 6.79 ppm, 1 H, d, J=7.47 Hz; 4.10 ppm, 1 H, d, J=14.06 Hz; 3.86 ppm, 1 H, d, J=14.50 Hz; 1.25 ppm, 9 H, s.

Provenance & Evidence