Bicarbonate Ion → N-(7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide

Temperature

75 °C

A mixture of 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one (740 mg, 2.25 mmol, Example 4), 2-methyl-2-propane-sulfinamide (819 mg, 6.76 mmol, Aldrich), and tetraethoxytitanium (6.07 mL, 29.3 mmol, Aldrich) in dry THF (15 mL) was heated at 75° C. for 24 hours under nitrogen atmosphere. The mixture was cooled to RT and brine and aqueous, saturated bicarbonate solution were added while rapidly stirring. After 1 h, the resulting suspension was filtered through celite, and the filter cake was washed with EtOAc. The filtrate was washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography on silica gel (0-20% EtOAc/hexanes) to afford the title product as an orange solid. MS m/z=423.8 [M+H]+. Calculated for C16H13BrClFN2O2S: 431.71.

1. temperatureThe mixture was cooled to RT
2. filtrationthe resulting suspension was filtered through celite
3. washthe filter cake was washed with EtOAc
4. washThe filtrate was washed with brine
5. dry with materialdried over MgSO4
6. customThe solvent was removed under reduced pressure
7. customthe remaining residue was purified by flash chromatography on silica gel (0-20% EtOAc/hexanes)

ORD record

ord-fcb6cadf3c334ff8a362511143d243b7

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921363B2