2-(1-Methyl-1H-pyrazol-4-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline → HCID 57843458, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(1-methyl-1H-pyrazol-4-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (9.22 mmol), N-(5-bromo-3-pyridinyl)-2,4-difluorobenzenesulfonamide (8.13 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.404 mmol) in 2M aqueous sodium carbonate (40 mL) and 1,4-dioxane (40 mL) was heated at 100° C. for 1 h. Upon cooling, the reaction mixture separated into two layers (aqueous and organic). The organic layer was partitioned between ethyl acetate (50 mL) and water (25 mL). The two aqueous layers were then combined and the pH was adjusted to ˜7 with 2N aqueous HCl. A solid precipitated and was filtered away from the solution. The solid was dried in vacuo and then desiccated over P2O5 to afford the title product (2.5 g, 64%). MS(ES)+ m/e 479 [M+H]+.

Provenance & Evidence