Methyl 2-chloro-6-methoxyisonicotinate → 2-(1-Ethylpropyl)-6-methoxyisonicotinic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6](Cl)[CH:5]=1>O1CCOCC1.C1COCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([CH:4]([CH2:9][CH3:8])[CH2:5][CH3:6])[CH:5]=1Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
Under argon, Pd(dppf) (83 mg, 101 μmol) is added to a solution of 2-chloro-6-methoxy-isonicotinic acid methyl ester (2.00 g, 9.92 mmol, see preparation of 2-isobutyl-6-methoxy-isonicotinic acid) in dioxane (30 mL). To this mixture, a solution of 1-ethyl-propyl zinkbromide (1.17 g, 9.92 mmol, 20 mL of a 0.5 M solution in THF) is added. The mixture is stirred at 85° C. for 16 h before the reaction is carefully quenched with water and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid methyl ester (1.17 g) as a pale yellow oil; LC-MS: tR=1.08 min; [M+1]+=238.03.
Aufarbeitung
- customis carefully quenched with water
- extractionextracted twice with EA
- dry with materialextracts are dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1
Quellen und Nachweise
- ORD-Eintrag
- ord-5cdf930e6d7143888052d2fe457f9de3
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08598208B2
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