Novel intermediate and process useful in the preparation of -(2-chlorophenyl)-methanone

Abstract

The present invention relates to novel compounds, (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone benzoate, and (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone toluate, which are useful intermediates for the preparation of the compound of Formula I: The present invention further relates to novel processes for preparing a crystalline compound, which is {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV.

What is claimed is: 
     
         1 . {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H- [1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV, prepared by a process comprising crystallizing dissolved {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone using a solvent and an anti-solvent wherein the solvent is isopropyl acetate and the anti-solvent is heptanes. 
     
     
         2 . {2-[1-(3,5 -bistrifluoromethylbenzyl)-5 -pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV according to  claim 1 , characterized by at least one of the following:
 a) a solid-state  13 C nuclear magnetic resonance spectrum comprising peaks at the following chemical shifts: 52.3±0.2 and 195.4±0.2 ppm;   b) an X-ray powder diffraction pattern comprising at least two peaks wherein one peak is 12.1±0.1° and the second peak is selected from the group consisting of 8.3±0.1°, 14.3±0.1°, 16.6±0.1°, 16.9±0.1°, and 18.5±0.1° in 2θ; or   c) an X-ray powder diffraction pattern comprising at least the following peaks: 8.3±0.1°, 12.1±0.1°, 16.6±0.1°, 16.9±0.1°, and 18.5±0.1° in 2θ.   
     
     
         3 . {2-[1-(3,5 -bistrifluoromethylbenzyl)-5 -pyridin-4-yl-1 H- [1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV according to  claim 2 , characterized by an X-ray powder diffraction pattern comprising at least the following peaks: 6.8±0.1°, 7.7±0.1°, 8.3±0.1°, 11.2±0.1°, 12.1±0.1°, 12.7±0.1°, 13.5±0.1°, 14.3±0.1°, 14.9±0.1°, 16.2±0.1°, 16.6±0.1°, 16.9±0.1°, 17.4±0.1°, 18.2±0.1°, 18.5±0.1°, 18.9±0.1°, 19.3±0.1°, 19.8±0.1°, 20.3±0.1°, 20.7±0.1°, 21.1±0.1°, 21.4±0.1°, 21.7±0.1°, 21.9±0.1°, 22.1±0.1°, 22.5±0.1°, 22.8±0.1°, 23.4±0.1°, 24.0±0.1°, 24.3±0.1°, 24.9±0.1°, 25.6±0.1°, 25.9±0.1°, 26.4±0.1°, 26.9±0.1°, 27.3±0.1°, 28.1±0.1°, 28.5±0.1°, 29.0±0.1°, 29.3±0.1°, 29.9±0.1°, 30.2±0.1°, 31.3±0.1°, 31.5±0.1°, 32.6±0.1°, 33.3±0.1°, 35.4±0.1°, 36.1±0.1°, 36.4±0.1°, and 36.8±0.1° in 2θ. 
     
     
         4 . A compound selected from the group consisting of (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3y1]methanone benzoate and (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone toluate. 
     
     
         5 . The compound of  claim 4  which is (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone benzoate.