Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 2-Fluoropyridine | HCID 9746 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 178510863 | HCID 178510863 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86675621 | HCID 86675621 | 81.2% |
Reaction Steps
Sodium hydride (63% mineral oil dispersion, 4.71 g) was added over 15 minutes to a solution of 1H-imidazol-4-ylacetonitrile (13.25 g) in N,N-dimethylformamide (46 mL) cooled to 0° C. Then, a solution of 2-fluoropyridine (12.61 g) in N,N-dimethylformamide (23 mL) was added thereto at room temperature, and the mixture was stirred at 100° C. for 5 hours. To the reaction solution, ice water was added, and methylene chloride was added. The formed solid was removed by suction filtration, and the organic layer was then separated and dried over anhydrous magnesium sulfate. Volatile matter was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the title compound (18.5 g, mixture with N,N-dimethylformamide).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946443B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-39f51d52edd94e8ebbac12d7431277ed |
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| Source note | uspto-grants-2015_02 |
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