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

Participants

Reaction Conditions

Reaction Steps

To propane-1-sulfonic acid (2,4-difluoro-phenyl)-amide (11, 1.5 g, 6.38 mmol) in 10 mL of tetrahydrofuran under an atmosphere of nitrogen and cooled in a −78° C. acetone/dry ice bath, lithium diisopropylamide (0.80 M in tetrahydrofuran, 24 mL, freshly prepared from n-butyllithium and diisopropylamine) was added. After 30 minutes, N,N-dimethyl-formamide (542 μL, 7.018 mmol) was added dropwise to the reaction. The reaction was stirred for 30 minutes at −78° C. and then allowed to warm to room temperature for 40 minutes. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and purified by silica gel column chromatography eluting with 5% ethyl acetate in hexane to give the desired compound as a light yellow solid (12, 300 mg, 18%). MS(ESI)[M−H+]−=262.3. Additional material was prepared similarly for the next step.

Provenance & Evidence