HuagongsheHuagongshe Chemistry Print Report · For research reference only
Allyltributylstannane → 3-Benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Allyltributylstannane | HCID 90628 | — |
| Reactant | 3-Benzyloxy-5-bromo-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide | HCID 58859131 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-Benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide | HCID 58859133 | 69.5% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
To a solution of 3-benzyloxy-5-bromo-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (138 mg) obtained in Example 161, Step 2 in dioxane (2.5 ml) were added tributyl-2-propenyltin (245 mg) and tetrakis(triphenylphosphine)palladium(0) (60 mg), and the mixture was stirred at 100° C. for 4 hr. The solvent was evaporated, toluene was added, and the mixture was concentrated again. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give 3-benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (89 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07211572B2 |
| Source dataset | uspto-grants-2007_05 |
| ORD ID | ord-d085fe6402f948148e7c87d65a936497 |
| Source note | uspto-grants-2007_05 |