Dichloromethane → HCID 86679723, Verbindung

HRID 711286

Reaktionsgleichung

Reaktionsgleichung von HRID 711286
[CH3:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][N:3]=1.Cl[C:18]1[C:25]([CH3:26])=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][N:19]=1.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+].C(OC(C)C)(=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:1][C:2]1[CH:7]=[C:6]([C:18]2[C:25]([CH3:26])=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][N:19]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

8

Edukt 5

HCID 6344DichloromethaneHCID 7915Isopropyl AcetateHCID 11430Potassium CarbonateHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 197106816-Chloro-5-methylpyridine-3-carbaldehyde

Produkt 1

HCID 86679723HCID 86679723, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customTo a 5-L four-necked flask equipped with an overhead stirrer
  2. temperaturecooled to 30° C
  3. customThe organic layer was separated
  4. washwashed with 10% NaCl (1120 g)
  5. additiontreated with activated charcoal (50 g) at 50° C. for 2 h
  6. temperaturebefore cooling to rt
  7. filtrationfiltered through Celite

Quellen und Nachweise

ORD-Eintrag
ord-a36e2845d6c54bea82f284b44f18b16b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181235B2

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