Potassium Carbonate → HCID 57586070, compound

Temperature

110 °C

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.

1. customMeOH that was previously degassed
2. temperatureThe reaction mixture was cooled down to room temperature
3. filtrationfiltered through celite
4. customThe aqueous layer was separated
5. washthe organic layer washed with water (50 mL)
6. washThe combined aqueous solutions were washed with diethyl ether (50 mL)
7. extractionacidified aqueous layer with HCl 5N and extracted with AcOEt
8. washwashed with brine (10 ml)
9. dry with materialdried over MgSO4
10. customevaporated down

ORD record

ord-8cb8a45c84724ae69c054310bf693138

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796280B2