Trimethylsilyldiazomethane → Methyl 4-iodo-2-methoxynicotinate

HRID 1034935

Reaktionsgleichung

Reaktionsgleichung von HRID 1034935
[I:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:11][CH3:12])[N:5]=[CH:4][CH:3]=1.[CH3:13][Si](C=[N+]=[N-])(C)C>CO>[I:1][C:2]1[C:7]([C:8]([O:10][CH3:13])=[O:9])=[C:6]([O:11][CH3:12])[N:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 184399404-Iodo-2-methoxypyridine-3-carboxylic acid

Produkt 1

HCID 58819970Methyl 4-iodo-2-methoxynicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Iodo-2-methoxynicotinic acid (800 mg, 2.87 mmol) is dissolved in MeOH (7 mL) and cooled at 0° C. Trimethylsilyldiazomethane (9 mL, 2M in hexane, 4.5 mmol) is added slowly over 20 minutes. The reaction mixture is brought to room temperature and stirred for 16 hours. The reaction mixture is concentrated and purified by silica gel column chromatography using hexane:ethyl acetate as eluent to afford the desired compound. 1H NMR 400 MHz (DMSO-d6) δ 7.88 (d, 1H, J=5.6 Hz), 7.34 (d, 1H, J=5.6 Hz), 4.12 (s, 3H), 3.84 (s, 1H); MS m/z 294.1 (M+1).

Aufarbeitung

  1. customis brought to room temperature
  2. concentrationThe reaction mixture is concentrated
  3. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-38bdaf2c97254d0e88dda5193b8834be
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546370B2

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