2-Chloro-5-pyridinesulfonyl chloride → (S)-6-chloro-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide

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Reaction Steps

2-chloropyridine-5-sulfonyl chloride (12 g, 56.6 mmol) was added to a solution of (S)-1,1,1-trifluoropropan-2-amine hydrochloride (7.8 g, 51.2 mmol) in pyridine (15 mL) at 0° C. The mixture was stirred at room temperature for 10 minutes and diluted with ethyl acetate (200 ml) and washed with 3 N aq. HCl (2×100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The solid was triturated with hexane (2×40 mL) and filtered to provide (S)-6-chloro-pyridine-3-sulfonic acid (2,2,2-trifluoro-1-methyl-ethyl)-amide as an off-white solid (11.84 g, 75%). 1H NMR (500 MHz, CDCl3): δ0.81 (1H, d, J=2.4 Hz), 8.18 (1H, dd, J=2.5 Hz, 2.6 Hz), 7.51 (1H, d, J=8.8 Hz), 4.92 (1H, br s), 4.08 (1H, m), 1.45 (3H, d, J=7.0 Hz).

Provenance & Evidence