Reaction #57811

ord-2d3835e24ca0434a96109c9e18f361e6

Reaction equation

c1ccc2c(-c3cccc4ccccc34)cccc2c1
1,1′-binaphthyl
O=C(c1ccncc1)c1cc(Cl)ccc1NS(=O)(=O)c1ccc(Br)cc1
4-Bromo-N-[4-chloro-2-(pyridine-4-carbonyl)-phenyl]-benzenesulfonamide
O.O=P([O-])([O-])[O-].[K+].[K+].[K+]
potassium phosphate tribasic monohydrate
C[C@@H]1CNC[C@H](C)O1
cis-2,6-dimethylmorpholine
C[C@@H]1CN(c2ccc(S(=O)(=O)Nc3ccc(Cl)cc3C(=O)c3ccncc3)cc2)C[C@H](C)O1
title compound
C[C@@H]1CN(c2ccc(S(=O)(=O)Nc3ccc(Cl)cc3C(=O)c3ccncc3)cc2)C[C@H](C)O1
N-[4-Chloro-2-(pyridine4-carbonyl)-phenyl]-4-(cis-2,6-dimethyl-morpholin-4-y1)-benzenesulfonamide

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherHPLC purification

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-(pyridine-4-carbonyl)-phenyl]-benzenesulfonamide 0.3 g (0.66 mmol), potassium phosphate tribasic monohydrate 0.91 g (3.96 mmol), rac-2,2′-bis diphenylphosphino)-1,1′-binaphthyl 0.12 g (0.198 mmol), cis-2,6-dimethylmorpholine 0.37 g (3.3 mmol) and Pd (dba)3 60 mg (0.066 mmol) in 6 ml dioxane, followed by work up and HPLC purification: LC-MSD, m/z for C24H24ClN3O4S [M+H]+: 486.0

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07420055B2uspto-grants-2008_09