Ethyl 2-chloroacetoacetate → Ethyl 7-methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 130666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130666
OC1C=CN2C(C(NC)=O)=C(C)N=C2C=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=1.Cl[CH:26]([C:32](=O)[CH3:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][N:21]2[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:32]([CH3:33])[N:24]=[C:20]2[CH:19]=1

Komponenten

5

Edukt 3

HCID 11858Ethyl 2-chloroacetoacetateHCID 108987152-Amino-4-MethoxypyridineHCID 178485487HCID 178485487, Verbindung

Produkt 1

HCID 53485249Ethyl 7-methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Note that 7-hydroxy-N,2-dimethylimidazo[1,2-α]pyridine-3-carboxamide 111-B was obtained by the following procedure. To a solution of 4-methoxypyridin-2-amine (prepared as in Org. Prep. & Proc. Int., 29, 1, 117-122, 1997) 2.8 g, 22.6 mmol in ethanol (100 ml) was added ethyl 2-chloro-3-oxobutanoate (6.2 ml, 45.2 mmol) and the resulting solution heated to reflux for 16 hours under a nitrogen atmosphere. The solvents were removed in-vacuo and the yellow solid was titrated with dichloromethane to extract the crude product. The dichloromethane extracts were concentrated and purified by flash chromatography (eluting with ethyl acetate) to yield ethyl 7-methoxy-2-methylimidazo[1,2-α]pyridine-3-carboxylate, 2 g, 38%, as a yellow solid.

Aufarbeitung

  1. customwas obtained by the following procedure
  2. temperaturethe resulting solution heated
  3. temperatureto reflux for 16 hours under a nitrogen atmosphere
  4. customThe solvents were removed in-vacuo
  5. extractionto extract the crude product
  6. concentrationThe dichloromethane extracts were concentrated
  7. custompurified by flash chromatography (eluting with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-43c864b3a04949b1b6a23bfda8b98c7a
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381824B2

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