Metalloenzyme inhibitor compounds as fungicides
US-2015291632-A1 · Oct 15, 2015 · US
US10669237B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10669237-B2 |
| Application number | US-201716462208-A |
| Country | US |
| Kind code | B2 |
| Filing date | Nov 17, 2017 |
| Priority date | Nov 18, 2016 |
| Publication date | Jun 2, 2020 |
| Grant date | Jun 2, 2020 |
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Provided herein is a process for the preparation of 4-((6-bromopyridin-3-yl)oxy)benzonitrile.
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What is claimed is: 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:
Two or more oxygen atoms · CPC title
attached in position 3 or 5 · CPC title
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