Quinolines and process for the preparation thereof

Patent metadata

Field	Value
Publication number	US-10144712-B2
Application number	US-201615543714-A
Country	US
Kind code	B2
Filing date	Jan 15, 2016
Priority date	Jan 15, 2015
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

The present invention discloses novel N-Heterocyclic compounds of formula A, [Formula A] And a ligand-enabled palladium-catalyzed process for preparation of novel N-Heterocyclic compounds of Formula A via C—H alkynylation of N-heterocycles with alkynyl halides.

First claim

The invention claimed is:

1. A heterocyclic compound of formula A

wherein,
R 1 is independently selected from the group consisting of hydrogen, alkyl (linear and branched), cycloalkyl, aryl, heterocyclyl, heteroaryl, alkylcycloalkyl, alkylaryl, alkylheterocyclyl, alkylheteroaryl, alkenyl, halogen, triflurometyl, nitro, amide, ester, cyano, alkoxy, alkylamino, arylamino, an inorganic support and a polymeric moiety;
R is selected from the group consisting of H, alkyl (linear, branched), cycloalkyl, aryl, heterocyclyl, heteroaryl, alkylcycloalkyl, alkylaryl, alkylheterocyclyl, alkylheteroaryl, alkenyl, halogen, triflurometyl, nitro, amide, ester, cyano, alkoxy, alkylamino, arylamino, an inorganic support and a polymeric moiety;
R 2 is H or the heterocyclic compound is 8-(3-(triisopropylsilyl)prop-2-ynyl)quinoline (3a).

2. The compound as claimed in claim 1 , wherein the heterocyclic compound of formula A is
8-(prop-2-yn-1-yl)quinoline (4a).

3. A process for preparation of heterocyclic compound 8-(prop-2-yn-1-yl)quinoline (4a) comprising the steps of:
a) stirring the reaction mixture of (bromoethynyl) triisopropylsilane (2), 8-methylquinolines (1a), Pd(OAc 2 ) 2 , 1,10-phenanthroline, Cu(OAc) 2 , and 1,2-dichloroethane (DCE) as a solvent for 15 hrs at a temperature of 110° C. to afford alkynylated product 8-(3-(triisopropylsilyl)prop-2-ynyl)quinoline (3a);
b) adding Tetra-n-butylammonium fluoride (TBAF) in THF to the alkynylated product of step (a) and diluting the mixture with tetrahydrofurane (THF) followed by stirring the reaction mixture at room temperature for 1 hr to afford desired desilated product 8-(prop-2-yn-1-yl)quinoline (4a).

4. The process as claimed in claim 3 , wherein said process is carried out at argon or nitrogen atmosphere.

Assignees

• Council Scient Ind Res

Inventors

• Ekambaram Balaraman
• Landge Vinod Gokulkrishna

Classifications

• B01J31/181

  Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine · CPC title

• C07D215/04

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms · CPC title

• C07D215/20

  Oxygen atoms · CPC title

• C07D215/12

  with substituted hydrocarbon radicals attached to ring carbon atoms · CPC title

• C07D215/18

  Halogen atoms or nitro radicals · CPC title