HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 56723596, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 5-bromopyridine-3-carboxylate | HCID 699336 | — |
| Reactant | 3-Chloro-4-methoxybenzeneboronic acid | HCID 3247522 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 56723596 | HCID 56723596 | 37.3% |
Reaction Steps
6.5 g of 3-chloro-4-methoxyphenylboronic acid, 5.0 g of methyl 5-bromonicotinate, 1.3 g of tetrakis(triphenylphosphine)palladium(0), and 22.6 g of Cs2CO3 were stirred in 325 ml of DMF and 65 ml of water for 3 h at 45° C. The reaction mixture was then poured into 750 ml of water and extracted three times using 300 ml of EA each. The combined organic layers were then washed twice using 150 ml of water each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP (gradient) yielded 2.4 g of the title compound, colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09018383B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-565735d6b27c44c6a6206665729d96d3 |
| Source note | uspto-grants-2015_04 |