HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cesium carbonate → Methyl 5-(3-chlorophenyl)nicotinate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | Methyl 5-bromopyridine-3-carboxylate | HCID 699336 | — |
| Edukt | 2-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 10037225 | — |
| Katalysator | HCID 178418397 | HCID 178418397 | — |
| Lösungsmittel | 1,2-Dimethoxyethane | HCID 8071 | — |
| Produkt | Methyl 5-(3-chlorophenyl)nicotinate | HCID 20099850 | 80,5% |
Reaktionsschritte
104 mg (0.09 mmol)Pd(PPh3)4, 1.5 g (6.29 mmol) of 3-chlorophenylboronic acid pinacol ester 2.86 ml (8.58 mmol) and 3M cesium carbonate solution were added under argon at room temperature to a solution of 1.24 g (5.72 mmol) methyl-5-bromo-pyridine-3-carboxylate in 45 ml dimethoxyethane and the mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and evaporated. The residue was taken up with ethyl acetate, washed with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.14 g (72%) of 5-(3-Chloro-phenyl)-nicotinic acid methyl ester
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07429605B2 |
| Quelldatensatz | uspto-grants-2008_09 |
| ORD ID | ord-48cf15a1bb314f92a712ee4b2305e794 |
| Quellennotiz | uspto-grants-2008_09 |