Hydrochloric Acid → N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamide

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Reaction Steps

To diisopropyl amine (0.210 mL, 1.49 mmol) in tetrahydrofuran (3 mL) was added n-butyllithium (2.50 M in hexane, 0.600 mL, 1.49 mmol) at −78° C. under an atmosphere of nitrogen. After 30 minutes, propane-1-sulfonic acid (2,4-difluoro-phenyl)-amide (9, 113 mg, 0.480 mmol) in tetrahydrofuran (2 mL) was added at −78° C. under am atmosphere of nitrogen. After 1 hour, N,N-dimethylformamide (0.050 mL, 0.64 mmol) was added. The reaction was stirred for 1 hour, then allowed to come to room temperature for 15 minutes. The reaction was poured into water, acidified with 1M HCl (aq.) to pH=1, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtrated. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a solid (10, 25 mg, 20%). MS (ESI) [M−H+]−=262.0.

Provenance & Evidence