Sodium Carbonate → Ethyl 4-chloro-6-(2,6-diethylphenyl)-2-methylnicotinate

HRID 251586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251586
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([Cl:11])=[CH:9][C:8](Cl)=[N:7][C:6]=1[CH3:13])[CH3:2].[CH2:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH3:24])[C:18]=1B(O)O)[CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:18]2[C:19]([CH2:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:15][CH3:16])=[N:7][C:6]=1[CH3:13])[CH3:2]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2786748Ethyl 4,6-dichloro-2-methylnicotinateHCID 18437832(2,6-Diethylphenyl)boronic acid

Produkt 1

HCID 59678345Ethyl 4-chloro-6-(2,6-diethylphenyl)-2-methylnicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4,6-dichloro-2-methyl-nicotinic acid ethyl ester (1.2 g, 5.1 mmol), 2,6-diethyl-phenyl boronic acid (2.18 g, 12.2 mmol), sodium carbonate (2 M aqueous solution, 12.2 mL, 24.4 mmol), and Pd(PPh3)4 (284 mg, 0.26 mmol) is refluxed in toluene for 48 hours and then cooled to room temperature. The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×50 mL). The organic Layers are combined, dried, and solvent removed. The crude product is purified by flash column (hexanes/ethyl acetate 8:1) to give 4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester. 1H NMR: (CDCl3) 7.26 (t, 1H), 7.18 (s, 1H), 7.13 (d, 2H), 4.47 (q, 2H), 2.62 (s, 3H), 2.28 (q, 4H), 1.44 (t, 3H), 1.04 (t, 6H).

Aufarbeitung

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with ethyl acetate (2×50 mL)
  3. customdried
  4. customsolvent removed
  5. customThe crude product is purified by flash column (hexanes/ethyl acetate 8:1)

Quellen und Nachweise

ORD-Eintrag
ord-b60b6c6c659b4622a8f6bec9514fc712
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863454B2

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