Water → HCID 21099479, compound

Participants

Reaction Steps

A mixture of 2-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzaldehyde (Example 176, 500 mg, 1.44 mmol), 2-methyl-2-propanesulfinamide (192 mg, 1.58 mmol) and titanium(IV) ethoxide (0.6 mL, 2.88 mmol) in tetrahydrofuran (7 mL) was heated to reflux for 4 hours. The cooled reaction mixture was partitioned between ethyl acetate and brine. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was taken up in methanol/dichloromethane (3:1, 16 mL) and sodium borohydride (424 mg, 8.64 mmol) added portionwise. After stirring at room temperature for 10 minutes, water and dichloromethane were added. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 50-90% ethyl acetate/isohexane, followed by recrystallisation to give the title compound as a white solid. δH (500 MHz, d6 DMSO): 8.11 (1H, d, J=7.8 Hz), 7.84-7.80 (4H, m), 7.73-7.66 (4H, m), 7.59-7.57 (1H, m), 7.45 (1H, d, J=16.4 Hz), 7.30 (1H, d, J=16.5 Hz), 7.23 (2H, t, J=8.8 Hz), 5.78 (1H, t, J=6.4 Hz), 4.45-4.35 (2H, m), 1.07 (9H, s).

Provenance & Evidence