Cesium carbonate → 4'-([3-Bromo-4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]thiomethyl)biphenyl-3-sulfonamide

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Reaction Conditions

Reaction Steps

Into a 50 mL round bottom flask was placed benzyl bromide of Step 7 (17 mg, 0.045 mmol) and cesium carbonate (0.017 g, 0.054 mmol) under an atmosphere of nitrogen in anhydrous DMF (0.68 mL). The solution was cooled to 0° C., evacuated and refilled with nitrogen several times. 4′-(Mercaptomethyl)biphenyl-3-sulfonamide (15 mg, 0.054 mmol) in 2 mL anhydrous DMF was added to reaction solution dropwise. The resulting solution was stirred at 0° C. for 1 h. The crude material was purified by preparative LCMS to give product as a white solid (4.6 mg 17%). 1H NMR (400 MHz, CD3OD): δ 8.15 (m, 1H), 7.86 (m, 2H), 7.59 (m, 4H), 7.38 (m, 4H), 5.54 (dd, J=18.6, 6.8 Hz, 1H), 3.72 (s, 2H), 3.68 (s, 2H), 3.42 (m, 1H), 3.35 (m, 1H). LCMS found for C23H22BrN2O5S3 (M+H)+: m/z=581, 583.

Provenance & Evidence