Reaction #57813

Reaction equation

potassium phosphate tribasic monohydrate

4-Bromo-N-[4-chloro-2-(pyridine4-carbonyl)-phenyl]-benzenesulfonamide

rac-2,2′-bis (diphenylphosphino)-1,1′-binaphthyl

piperazine-1-carboxylic acid tert-butyl ester

→

title compound

N-[4-Chloro-2(pyridine-4-carbonyl)-phenyl]-4-piperazin-1-yl-benzenesulfonamide

Solvents

dioxane

Conditions

Procedure

The title compound was prepared according to the general procedure for the synthesis of heterocyclyl and heteroaryl substituted phenylsulfonyl derivatives previously described, using 4-Bromo-N-[4-chloro-2-(pyridine4-carbonyl)-phenyl]-benzenesulfonamide 0.1 g (0.22 mmol), potassium phosphate tribasic monohydrate 0.30 g (1.2 mmol), rac-2,2′-bis (diphenylphosphino)-1,1′-binaphthyl 0.02 g (0.032 mmol), piperazine-1-carboxylic acid tert-butyl ester 0.18 g (1 mmol) and Pd (II) trifluoroacetate 10 mg (0.01 mmol) in 6 ml dioxane. The compound was then deprotected to yield free amine using dichloromethane (2 mL) with trifluoroacetic acid (3 mL) for 1 hour at room temperature. The crude material was concentrated under vacuo, purified by HPLC, to give yellow solid.

Source