Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-(p-Hydroxyphenyl)imidazole | HCID 82315 | — |
| Reactant | HCID 12042979 | HCID 12042979 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 9951410 | HCID 9951410 | 55.6% |
Reaction Steps
To DMSO (5 mL) was added 2-(1,3-benzodioxol-5-yloxy)-6-fluoropyridine (1.3 g, 5.3 mmol), 1-(4-hydroxyphenyl)imidazole (0.92 mL, 5.8 mmol), and cesium carbonate (1.82 g, 5.6 mmol). After heating at 90° C. for 18 hour, the reaction was partitioned with water and ethyl acetate. The organic layer was washed with water and brine, dried (Na2SO4) and the solvent was removed in vacuo. The residue was chromatographed on silica with ethyl acetate/hexane to get 1.1 g of 2-(1,3-benzodioxol-5-yloxy)-6-[4-(1H-imidazol-1-yl)phenoxy]pyridine; NMR (CDCl3) δ 7.8 (s, 1H), 7.7 (t, 1H), 7.35 (d, 2H), 7.2 (m, 3H), 6.75 (d, 1H), 6.6 (m, 3H), 6.55 (m, 2H), 5.9 (s, 2H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06525051B2 |
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| Source dataset | uspto-grants-2003_02 |
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| ORD ID | ord-cc5315df5ee4484da2f233ce00ce58b3 |
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| Source note | uspto-grants-2003_02 |
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