Diisopropylethylamine → HCID 58980644, Verbindung

HRID 735803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735803
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:8]=[C:7]([Br:15])[C:6]=1[OH:16])[CH3:2].[CH:18](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C.CO>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[N:8]=[C:7]([Br:15])[C:6]=1[O:16][CH3:18])[CH3:2]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 58980648Ethyl 2-bromo-6-(1,1-dimethylethyl)-3-hydroxy-4-pyridinecarboxylate

Produkt 1

HCID 58980644HCID 58980644, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21959252Acetonitrile methanolLösungsmittel

Versuchsvorschrift

To a solution of the above bromopyridine (2.74 g, 9.07 mmol) in acetonitrile/methanol (9:1, 33 mL) was added N,N-diisopropylethylamine (2.50 mL, 14.2 mmol) followed by (trimethylsilyl)diazomethane (2.0M in hexane, 7.0 mL, 14.2 mmol). The red solution was stirred 0.5 h at room temperature then concentrated in vacuo. The residue was dissolved in methylene chloride, washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-bromo-6-tert-butyl-3-methoxy-isonicotinic acid ethyl ester (2.65 g, 93%) as a red oil which was utilized without further purification.

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d3959b4ecab84203864e32467d187703
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592332B2

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