Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 3-(1,3,2-Dioxaborinan-2-yl)pyridine | HCID 4198005 | — |
| Reactant | Methyl 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate | HCID 21919123 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 21919148 | HCID 21919148 | 85% |
Reaction Steps
To a solution of methyl 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate (316 mg, 0.6220 mmol) in toluene (7.1 ml) were added tetrakistriphenylphosphine palladium (22 mg, 0.0190 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 0.81 ml), lithium chloride (53 mg, 1.2502 mmol) and ethanolic solution (1.3 ml) of pyridine-3-boronic acid 1,3-propanediol cyclic ester (151 mg, 0.9320 mmol) and the mixture was heated with stirring at 95° C. for 16 hours. The reaction solution was diluted with ethyl acetate (100 ml), washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (231 mg, 0.5286 mmol, 85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07122543B2 |
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| Source dataset | uspto-grants-2006_10 |
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| ORD ID | ord-d1a8c26364814958a50cceb0c7d47497 |
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| Source note | uspto-grants-2006_10 |
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