Potassium Phosphate, Tribasic → HCID 56971353, compound

Participants

Reaction Steps

6-chloro-4-(4-chlorophenyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazin-4-ol 1,1-dioxide (0.180 g, 0.514 mmol), pyridine-4-boronic acid (0.126 g, 1.03 mmol), Bis(dibenzylideneacetone)palladium(0) (0.0296 g, 0.0514 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (0.0980 g, 0.206 mmol) and Potassium phosphate (0.327 g, 1.54 mmol) were combined in microwave vial and flushed with argon. 1-Butanol (10 mL) was added and the reaction was microwaved on 150 watts, 120° C. for 30 minutes. LCMS indicated the product of coupling. The solvent was evaporated and the residue was purified using column chromatography on silica gel (40 g Analogix column, gradient 10% EA in hexane to 100% EA in hexane over 25 minutes) to give the title compound (110 mg, 52%). LCMS: (FA) ES+ 393, 395. 1H NMR (400 MHz, d6-DMSO) δ: 8.59 (dd, J=4.54, 1.64 Hz, 2H), 8.36 (d, J=0.94 Hz, 1H), 7.68 (dd, J=4.52, 1.68 Hz, 2H), 7.50-7.41 (m, 3H), 6.57 (s, 1H), 7.39-7.27 (m, 2H), 3.75-3.59 (m, 2H).

Provenance & Evidence