Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Dichloromethane | HCID 6344 | — |
| Edukt | Isopropyl Acetate | HCID 7915 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 2-Methylpyridine-4-boronic acid pinacol ester | HCID 16414274 | — |
| Edukt | 6-Chloro-5-methylpyridine-3-carbaldehyde | HCID 19710681 | — |
| Katalysator | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Produkt | HCID 86679723 | HCID 86679723 | — |
Reaktionsschritte
To a 5-L four-necked flask equipped with an overhead stirrer, a thermocouple and a condenser was charged with 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (34b, 1120 mmol), 6-chloro-5-methylnicotinaldehyde (34c, 174.3 g, 1120 mmol), Pd(dppf)Cl2.CH2Cl2 (4.57 g, 5.6 mmol), K2CO3 (309.6 g, 2240 mmol), and iso-propyl acetate (1120 mL)/water (1120 mL). The mixture was stirred at 75° C. for 4 h, and cooled to 30° C. The organic layer was separated, washed with 10% NaCl (1120 g), and treated with activated charcoal (50 g) at 50° C. for 2 h before cooling to rt and filtered through Celite. Concentration of the filtrate to almost dryness afforded the crude 2′,3-dimethyl-[2,4′-bipyridine]-5-carbaldehyde (34d) as a brown oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US09181235B2 |
|---|
| Quelldatensatz | uspto-grants-2015_11 |
|---|
| ORD ID | ord-a36e2845d6c54bea82f284b44f18b16b |
|---|
| Quellennotiz | uspto-grants-2015_11 |
|---|
