Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | N-(2,6-dichloro-pyridin-3-yl)-4-methoxy-benzamide | HCID 58220150 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58220156 | HCID 58220156 | 59.1% |
Reaction Steps
N-(2,6-Dichloro-pyridin-3-yl)-4-methoxy-benzamide (3.86 g, 13.0 mmol) and K2CO3 (1.80 g, 13 mmol) were combined in DMF (15 mL) and heated by microwave to 160° C. for 30 minutes. The resulting mixture was poured into water (100 mL) causing the formation of a precipitate which was collected by filtration and washed with additional water before drying overnight in vacuo. The resulting solid was purified with silica gel flash chromatography (0-60% EtOAc in hexanes) to afford 5-chloro-2-(4-methoxy-phenyl)-oxazolo[5,4-b]pyridine (2.0 g, 7.67 mmol, 59.1% yield) which was used in subsequent reactions without further purification. ES MS (M+H+)=261.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08530483B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-066f0a9fb8014c528d829895a2a6db74 |
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| Source note | uspto-grants-2013_09 |
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