Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Hydroxypyridine | HCID 7971 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Chloro-2-pyridinecarbonitrile | HCID 693342 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 55209004 | HCID 55209004 | 93% |
Reaction Steps
4-Chloro-2-pyridine carbonitrile (1.0 g, 7.2 mmol, 1.0 eq), 3-hydroxypyridine (686 mg, 7.21 mmol, 1.00 eq) and K2CO3 (1.2 g, 8.7 mmol, 1.2 eq) were dissolved in DMF (10 mL) and heated in a microwave for 15 minutes at 150° C. The reaction was cooled, diluted with EtOAc and washed with H2O (3×). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 1.32 g (93%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.62 (d, J=5.8 Hz, 1H), 8.56 (m, 2H), 7.79 (d, J=2.4 Hz, 1H), 7.75 (dt, J=8.4, 1.4 Hz, 1H), 7.55 (dd, J=8.3, 4.7 Hz, 1H), 7.27 (dd, J=5.7, 2.4 Hz, 1H); ES-MS [M+1]+: 198.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08598345B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-73d310257bf3467ebdd83528767d406f |
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| Source note | uspto-grants-2013_12 |
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