HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → Methyl 3-[6-(4-fluorophenyl)pyridin-3-yl]prop-2-enoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | 3-(6-Bromopyridin-3-yl)acrylic acid methyl ester | HCID 71427582 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Methyl 3-[6-(4-fluorophenyl)pyridin-3-yl]prop-2-enoate | HCID 68821839 | — |
Reaction Steps
A mixture of 2980 mg (12.31 mmol) of 3-(6-bromopyridin-3-yl)acrylic acid methyl ester, 2067 mg (14.77 mmol) of 4-fluorophenylboronic acid, 138.2 mg (0.61 mmol) of palladium(II)acetate, 322.9 mg (1.23 mmol) of triphenylphosphane and 14.7 ml of a 1M sodium carbonate solution in 73 ml of toluene and 20 ml of ethanol was heated under reflux for 1.5 h. After cooling, the mixture was poured onto water and extracted with ethyl acetate. The organic phases were evaporated and residue purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1). Yield: 2.4 g (76%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642620B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-be80b9617cb04a7f8fb3a2c9e0a8cdd0 |
| Source note | uspto-grants-2014_02 |