Tetrahydrofuran → HCID 90373278, compound

Participants

Reaction Conditions

Reaction Steps

To a 1000 mL, 3-neck, round-bottomed flask equipped with an internal temperature probe was added 1-(6-bromo-3-fluoro-4-(triethylsilyl)pyridin-2-yl)-2-fluoroethanone (35 g, 100 mmol), THF (350 mL), (R)-2-methylpropane-2-sulfinamide (AK Scientific; 25.4 g, 210 mmol) and titanium (iv) ethoxide (Aldrich; 51.7 mL, 250 mmol). The solution was heated and stirred at 30° C. for 15 h and then at 40° C. for 2 h. The solution was allowed to cool to rt and then brine (200 mL) was added followed by EtOAc (200 mL). A white precipitate formed. The solution was filtered through Celite (600 mL medium fritted funnel) and the filtercake was washed with EtOAc. The filtrate was washed with brine, dried (Na2SO4) and concentrated to afford the crude product as a yellow semi-solid. The material was dissolved in 20% EtOAc/hexane (300 mL) and washed with water (2×100 mL) and brine (100 mL) and then dried and concentrated to afford (R,E)-N-(1-(6-bromo-3-fluoro-4-(triethylsilyl)pyridin-2-yl)-2-fluoroethylidene)-2-methylpropane-2-sulfinamide (37.8 g, 83 mmol, 84% yield) as a yellow oil which was carried on directly. MS m/z=453.0 [M+H]+. Calculated for C17H27BrF2N2OSSi: 452.1.

Provenance & Evidence