To a solution of 2,4,6-tris(4-bromophenyl)-1,3,5-triazine (1.00 g, 1.83 mmol, 1.00 equiv) in 150 mL of dry THF, butane;lithium (504 mg, 3.15 mL, 7.88 mmol, 2.50M, 4.30 equiv) was added dropwise at –78 °C for 20 minutes. The solution was stirred at this temperature for 6 hours before a solution of (NE)-N-diazo-4-methylbenzenesulfonamide (1.70 g, 8.62 mmol, 4.71 equiv) in 50 mL of dry THF was added. After stirring for 2 days at 21°C, the mixture was carefully quenched with water. The aqueous phase was separated by adding total saline and diethyl ether, a formed precipitate was filtered off and the aqueous phase was extracted with diethyl ether. The combined organic phases were washed with water and saturated saline solution, dried over magnesium sulfate and the solvent then removed at reduced pressure. The filtered precipitate and the crude product were heated in dichloromethane to dissolve, insoluble components were filtered off and the filtrate passed through a filter column to give 428 mg (0.990 mmol) of a light beige solid.
