4-((6-bromopyridin-3-yl)oxy)benzonitrile and processes of preparation
Provided herein is a process for the preparation of 4-((6-bromopyridin-3-yl)oxy)benzonitrile.
1. A method of making a compound of Formula I
comprising the step of contacting a compound of Formula II
with a dehydrative brominating reagent.
2. The method of claim 1 , further comprising a solvent selected from the group including acetonitrile, toluene, DMF, DCM, and dioxane.
3. The method of claim 1 wherein the dehydrative brominating reagent may be selected from the group including POBr 3 , PBr 3 , PBr 5 , P 2 O 5 combined with tetrabutylammonium bromide, triphenylphosphine combined with N-bromosuccinimide, and mixtures thereof.
4. The method of claim 1 wherein the dehydrative brominating reagent may be selected from POBr 3 , PBr 5 , and mixtures thereof.
5. The method of claim 1 , wherein the contacting is carried out between about 50° C. and about 200° C.
6. The method of claim 1 , further comprising the step of:
contacting a compound of Formula III
with a compound of Formula IV and a base
to prepare the compound of Formula II.
7. The method of claim 6 wherein the base is selected from the group including cesium carbonate, potassium carbonate, sodium hydride, potassium hydride, sodium hydroxide, and potassium hydroxide.
8. The method of claim 6 further comprising a solvent selected from the group including dimethylsulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide, sulfolane, and N-methyl-2-pyrrolidone.
9. The method of claim 6 wherein the contacting is carried out between about 50° C. and about 200° C.
10. A compound consisting of: