HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → 4-Acetylamino-3-chloro-6-(4-chloro-2-fluoro-5-methoxyphenyl)pyridine-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 1,4-Bis(diphenylphosphino)butane | HCID 82124 | — |
| Reactant | Methyl 4-acetamido-3,6-dichloropyridine-2-carboxylate | HCID 22677481 | — |
| Reactant | 2-(4-Chloro-2-fluoro-5-methoxyphenyl)-[1,3,2]-dioxaborinane | HCID 66954701 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 4-Acetylamino-3-chloro-6-(4-chloro-2-fluoro-5-methoxyphenyl)pyridine-2-carboxylic acid methyl ester | HCID 68600593 | 75% |
Reaction Steps
A solution of 4-acetylamino-3,6-dichloropyridine carboxylic acid methyl ester (4.3 g, 0.016 mol), 2-(4-chloro-2-fluoro-5-methoxyphenyl)-[1,3,2]-dioxaborinane (4.5 g, 0.018 mol), cesium fluoride (3.5 g, 0.025 mol), and 1,4-bis(diphenylphosphino)butane (0.360 g, 0.0016 mol) in acetonitrile (100 mL) was degassed with nitrogen for 15 minutes before palladium acetate (0.180 g, 0.0016 mol) was added and the solution heated under reflux for 18 hours. Water (150 mL) was added and the resulting solid collected and dried to give 4-acetylamino-3-chloro-6-(4-chloro-2-fluoro-5-methoxyphenyl)pyridine-2-carboxylic acid methyl ester (4.5 g, 0.012 mol): mp 180-182° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07498468B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-9d5521e78560442b906e15943c2ba77c |
| Source note | uspto-grants-2009_03 |