Potassium Carbonate → 5-(4-chloro-2-(pyridin-4-yl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A pressure vessel was charged with 5-(2-bromo-4-chlorophenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (80 mg, 0.166 mmol), potassium carbonate (115 mg, 0.832 mmol), pyridin-4-ylboronic acid (30.7 mg, 0.250 mmol), tetrakis(triphenylphosphine)palladium(0) (19.23 mg, 0.017 mmol), dioxane (1109 μl) and water (555 μl). The reaction mixture was heated in a microwave at 100° C. for 30 min. The mixture was then cooled to room temperature and the organic layer was separated from the aqueous layer by pipet. The resulting organic layer was then injected as is onto a reverse phase HPLC for purification (Column: Xbridge 19×100 mm, 5 μm, Waters, Milford, Mass., Flow rate: 40 mL/min, Mobile phase: 0.1% TFA in ACN and water). The fractions containing product were dried under a vacuum to provide 5-(4-chloro-2-(pyridin-4-yl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (5 mg, 0.01 mmol) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.54 (s, 2H) 7.04 (d, J=5.98 Hz, 2H) 7.36-7.41 (m, 1H) 7.46 (d, J=8.76 Hz, 1H) 7.51-7.60 (m, 2H) 7.63-7.70 (m, 3H) 8.09 (d, J=8.33 Hz, 1H) 8.16 (s, 1H) 8.26 (d, J=5.56 Hz, 2H) 8.39 (d, J=1.71 Hz, 1H); m/z (ESI) 479.0 (M+H)+.

Provenance & Evidence