2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1H-tetrazol-1-yl)propan-2-ols and processes for their preparation

1. A method of making compounds of the Formula IV:

by contacting a compound of Formula III with R 2 —CN,

wherein R 2 is selected from —CO 2 Et, —C(O)Me, —C(O)Ph, and —SO 2 (4-MePh).

2. The method of claim 1 , wherein the step of contacting compounds of Formula III with R 2 —CN is carried out between 90° C. and 130° C.

3. The method of claim 1 , further comprising the step of contacting a compound of Formula II with sodium azide and a solvent

4. The method of claim 3 , wherein the solvent is selected from dimethylformamide and methanol.

5. The method of claim 3 , wherein the step of contacting the compound of Formula II with sodium azide and a solvent is carried out between 40° C. and 60° C.

6. The method of claim 3 , further comprising the step of contacting the compound of Formula I with trimethylsulfoxonium iodide and a base

7. The method the claim 6 , wherein the base is sodium hydride.

8. The method of claim 1 , wherein R 2 is —CO 2 Et, further comprising the steps of:

contacting a compound of Formula IV with sodium hydroxide forming a mixture; and

contacting the mixture with hydrochloric acid.

9. The method of claim 1 , wherein R 2 is one of —C(O)Me and —C(O)Ph, further comprising the step of:

contacting the compound of Formula IV with a base and a solvent.

10. The method of claim 9 , wherein the solvent is ethanol.

11. The method of claim 9 , wherein base is one of sodium hydroxide and piperidine.

12. The method of claim 9 , wherein the step of contacting the compound of Formula IV with the base and the solvent is carried out between 60° C. and 90° C.

13. The method of claim 1 , wherein R 2 is —SO 2 (4-MePh), further comprising the step of:

contacting the compound of Formula IV with Zn and an acid.

14. The method of claim 13 , wherein the acid is acetic acid.