Potassium Phosphate, Tribasic → 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 5-bromo-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide (Intermediate W) (0.508 g, 1.395 mmol), (2-chloro-4-(trifluoromethyl)phenyl)boronic acid (0.469 g, 2.092 mmol), potassium phosphate (0.888 g, 4.18 mmol), and 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(ii) chloride (0.099 g, 0.139 mmol). The vial was sealed with a septum cap and flushed with N2. Dioxane (3.49 mL) and water (1.162 mL) were added and the mixture was sparged for 5 min with N2. The mixture was heated in a microwave at 90° C. for 30 min. The resulting mixture was diluted with EtOAc (5 mL) and decanted from insoluble solids. The resulting solution was concentrated for purification by MPLC. The residue was taken up in minimal CH2Cl2 and absorbed onto a 5 g loading cartridge and passed through a silica gel column (12 g) using a 98:2 Heptane:EtOAc (with 5% EtOH additive) to 100% EtOAc (5% EtOH additive) gradient to afford 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide (0.485 g, 1.046 mmol) as a orange amorphous solid.

Provenance & Evidence