Potassium Acetate → {6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid

Participants

Reaction Conditions

Reaction Steps

N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide (1 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (0.98 g), potassium acetate (1.03 g) and Pd(dppf)Cl2 (0.256 g) were weighed to a 10-20 ml microwave vial and 1,4-dioxane (10 ml) was added. The reaction was heated at 80° C. for a total of 2 h in the microwave. Further 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (0.489 g), potassium acetate (0.516 g) and Pd(dppf)Cl2 (0.128 g) were added and the reaction was heated at 90° C. for a total of 1.5 h in the microwave. The reaction was filtered through a hydrophobic frit then evaporated to dryness. The residue was purified on the ISCO companion using an 80 g silica cartridge, and a gradient of 2-8% methanol in DCM (containing 1% ammonia) over 25 mins. Pure fractions were combined and evaporated to dryness, then dried on the vacuum line to give title compound (439 mg).

Provenance & Evidence