Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 6-Bromo-3,4-dimethoxybenzaldehyde | HCID 79351 | — |
| Reactant | 3-Pyridinylboronic acid | HCID 2734378 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 54912235 | HCID 54912235 | — |
Reaction Steps
A mixture of 2-bromo-4,5-dimethoxybenzaldehyde (0.368 g, 1.5 mmol), pyridin-3-ylboronic acid (0.246 g, 2.0 mmol), Pd(PPh3)4 (0.173 g, 0.150 mmol), and cesium carbonate (0.977 g, 3 mmol) were suspended in dioxane (4 mL) and water (1 mL). The mixture was heated to 140° C. in a microwave for 1 h. The reaction vessel was allowed to cool to ambient temperature, diluted with ethyl acetate (˜25 mL), filtered through a bed of Celite, and conc. in vacuo to afford the aldehyde which was purified via SiO2 chromatography (40 g) using ethyl acetate/hexanes (5:1) as eluent to afford the title compound as a white solid (0.340 g, 93%); m/z 244.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08901307B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-5afc426eb2924b068ed9ee8715f682c3 |
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| Source note | uspto-grants-2014_12 |
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