Trimethylsilyldiazomethane → Methyl 4-iodo-2-methoxynicotinate

HRID 457551

Reaktionsgleichung

Reaktionsgleichung von HRID 457551
[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>[CH3:13][O:9][C:8](=[O:10])[C:7]1[C:2]([I:1])=[CH:3][CH:4]=[N:5][C:6]=1[O:11][CH3:12]

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

Versuchsvorschrift

To a solution of 4-iodo-2-methoxy-nicotinic acid (1.7 g, 6.1 mmol) in 50 mL of methanol (50 ml) was added trimethylsilyldiazomethane (15 mL of a 2M solution in hexanes, 30 mmol). The mixture was stirred at ambient temperature overnight, then concentrated. The crude product was purified by flash column chromatography on silica (eluent: hexanes-ethyl acetate-triethylamine 100-10-1, then 70-30-1). 1.685 g colorless solid were isolated (94%). 1H NMR (500 MHz, acetone-d6) δ 7.93 (d, J=5.4 Hz, 1H), 7.50 (d, J=5.4 Hz, 1H), 3.92 (s, 3H), 3.90 (s, 3H);

Aufarbeitung

  1. concentrationconcentrated
  2. customThe crude product was purified by flash column chromatography on silica (eluent

Quellen und Nachweise

ORD-Eintrag
ord-cdf895af4f7945b7a035347b5b4d0e3b
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189716B2

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