Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | HCID 69094001 | HCID 69094001 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69093841 | HCID 69093841 | 31% |
Reaction Steps
To a solution of 2-(5-bromo-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)pyridine (I-16, 0.95 g, 2.9 mmol) in N,N-dimethylformamide (9.5 mL) was added potassium cyanide (0.928 g, 14.3 mmol). After heating the solution at 100° C. for 22 h, the solution was diluted with ethyl acetate (125 mL) and water (100 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organics were combined, washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to give the crude product as an orange oil. Purification by silica gel chromatography (0-15% ethyl acetate in dichloromethane) gave 1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-5-carbonitrile, I-33 (250 mg, 0.90 mmol, 31% yield) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09061030B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-95729f754c7e40b78e6c43fea2addaec |
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| Source note | uspto-grants-2015_06 |
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