Potassium Carbonate → HCID 57586070, compound

Participants

Reaction Conditions

Reaction Steps

2-chloro-N-(3-chloropyrazin-2-yl)benzenesulfonamide (2.2 g; 7.23 mmol; 1.00 eq.) and 4-hydroxymethyl benzene boronic acid (1.21 g; 7.96 mmol; 1.10 eq.) were dissolved in 48 mL of a 1:1 mixture of Dioxane:MeOH that was previously degassed. Potassium carbonate (2.75 g; 19.89 mmol; 2.75 eq.) and triphenylphosphine (284.58 mg; 1.08 mmol; 0.15 eq.) were added to the reaction mixture under nitrogen, followed by palladium II (81.19 mg; 0.36 mmol; 0.05 eq.). The reaction mixture was then heated at 110° C. under N2 for 30 minutes. The reaction mixture was cooled down to room temperature, diluted with diethyl ether (50 mL) and water (25 mL) and filtered through celite. The aqueous layer was separated and the organic layer washed with water (50 mL). The combined aqueous solutions were washed with diethyl ether (50 mL), then acidified aqueous layer with HCl 5N and extracted with AcOEt. The organic extracts were combined, washed with brine (10 ml), dried over MgSO4 and evaporated down to give the pure 2-chloro-N-{3-[4-(hydroxymethyl)phenyl]pyrazin-2-yl}benzene sulfonamide as a yellowish solid (2.5 g, 91% yield, 98% HPLC purity). This compound was used as such for the next reaction.

Provenance & Evidence