HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → 6-Chloro-2-oxo-4-pent-1-enyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (1E)-(Pent-1-en-1-yl)boronic acid | HCID 5702651 | — |
| Reactant | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Reactant | 6-Chloro-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester | HCID 21020252 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | 6-Chloro-2-oxo-4-pent-1-enyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester | HCID 69659288 | 70.8% |
Reaction Steps
A solution of 11 (0.10 g, 0.19 mmol), E-penten-1-ylboronic acid (44.0 mg, 0.38 mmol), tetrakis(triphenylphosphine)palladium (22.0 mg, 0.023 mmol), and NaHCO3 (41.0 mg, 0.38 mmol) in 1:1 DME/H2O (3 mL) was heated at 100° C. for 1 h. The reaction was allowed to cool to room temperature, diluted with H2O, extracted with EtOAc, dried (Na2SO4), filtered, and concentrated. Chromatography (SiO2, 3:1 Hex/EtOAc) gave 12 (43.0 mg, 51%) as a colorless film.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07019141B2 |
| Source dataset | uspto-grants-2006_03 |
| ORD ID | ord-c7849a97140740f0b243db2fa0970248 |
| Source note | uspto-grants-2006_03 |