2,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamide → (2,6-Dichloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone
Reaktionsgleichung
[Cl:1][C:2]1[N:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Li]>O1CCCC1>[Cl:1][C:2]1[C:3]([C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[O:5])=[CH:10][CH:11]=[C:12]([Cl:14])[N:13]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 2,6-Dichloro-N-methoxy-N-methyl-nicotinamide (503.3 mg, 2.141 mmol, Example 1) in anhydrous tetrahydrofuran (8 mL) was added a solution of freshly prepared 2-methoxyphenyl lithium (3-5 equiv, from above) and the reaction was stirred at −78° C. for 30-60 mins until the complete consumption of starting material. The resulting mixture was quenched with aqueous ammonium chloride solution, extracted with ethyl acetate, washed with saturated sodium chloride, dried over sodium sulfate and evaporated in vacuo. The residue was purified on silica gel with hexanes/ethyl acetate to give (2,6-Dichloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone as a light brown waxy solid (314.3 mg, 52% yield). HRMS, observed: 281.0023, Calcd for M+: 281.0010.
Aufarbeitung
- customThe resulting mixture was quenched with aqueous ammonium chloride solution
- extractionextracted with ethyl acetate
- washwashed with saturated sodium chloride
- dry with materialdried over sodium sulfate
- customevaporated in vacuo
- customThe residue was purified on silica gel with hexanes/ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-2f53521dbb114570a3c6959688798de8
- Quelldatensatz
- uspto-grants-2008_09
- Patentnummer
- US07423051B2
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