IP Library › Patent Application 16462183
Patent Application
App. No. 16/462,183

4-(6-(2-(2,4-DIFLUOROPHENYL)-1.1-DIFLUORO-2-HYDROXY-3-(5-MERCAPTO-1H-1,2,4-TRIAZOL-1-YL)PROPYL)PYRIDIN-3-YL)OXY)BENZONITRILE AND PROCESSES OF PREPARATION

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Quick Facts
Patent No.
US None
App. No.
16/462,183
Abstract

Provided herein is a process for the preparation of 4-(6-(2-(2,4-difluorophenyl)-1.1-difluoro-2-hydroxy-3-(5-mercapto-1H-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile.

Claims (19)

1 . A method of making a compound of Formula I

comprising the step of contacting a compound of Formula II

wherein X is Cl, Br or I;

with an alkanedithiol, a copper salt and a base.

2 . The method of claim 1 , wherein the copper salt may be selected from the group including CuSO 4 , CuCl 2 , CuBr 2 , Cu(acac) 2 , Cu(OAc) 2 , Cu(OH) 2 , CuO, and mixtures thereof.

3 . The method of claim 1 , wherein the base is selected from the group including a metal carbonate, a metal alkoxide, a metal phosphate, and a metal hydroxide.

4 . The method of claim 1 , wherein the base is selected from the group including potassium carbonate, sodium carbonate, and cesium carbonate.

5 . The method of claim 1 further comprising a solvent selected from the group including acetonitrile, N,N-dimethylacetamide, dimethylsulfoxide, N,N-dimethylformamide, N-methyl-2-pyrrolidone, sulfolane, and mixtures thereof, and mixtures of any of these solvents with water.

6 . The method of claim 1 wherein the contacting is carried out between about 25° C. and about 200° C.

7 . The method of claim 1 wherein the contacting is carried out between about 50° C. and about 150° C.

8 . The method of claim 1 , further comprising the step of contacting a compound of Formula III

with a halogenating agent and a free radical initiator compound to prepare the compound of Formula II, wherein X is a Cl, Br, or I.

9 . The method of claim 8 , wherein the halogenating agent may be selected from the group including NBS, NCS, NIS, Br 2 , Cl 2 , I 2 , 1,3-dibromo-5,5-dimethylhydantoin, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, and NaBr/H 2 O 2 .

10 . The method of claim 8 , wherein the free radical initiator compound may be selected from benzoyl peroxide or azobisisobutyronitrile (AIBN).

11 . The method of claim 8 further comprising a solvent selected from the group including acetonitrile, N,N-dimethylformamide, N-methyl-2-pyrrolidone, toluene, and ethyl acetate.

12 . The method of claim 8 wherein the contacting is carried out between about 25° C. and about 150° C.

13 . The method of claim 8 wherein the contacting is carried out between about 50° C. and about 125° C.

14 . A compound consisting of:

wherein X=Cl, Br or I.