Ethyl 2-chloroacetoacetate → Ethyl 8-chloro-2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate

HRID 931020

Reaktionsgleichung

Reaktionsgleichung von HRID 931020
[Cl:1][C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl[CH:14]([C:20](=O)[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>CC(O)C>[Cl:1][C:2]1[C:3]2[N:4]([C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:21])[N:12]=2)[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Komponenten

5

Edukt 3

HCID 11858Ethyl 2-chloroacetoacetateHCID 516892Sodium BicarbonateHCID 6072483-Chloro-5-(trifluoromethyl)-2-pyridinamine

Produkt 1

HCID 118379039Ethyl 8-chloro-2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylateAusbeute 17,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 3-chloro-5-(trifluoromethyl)pyridin-2-amine (2 g), ethyl 2-chloro-3-oxobutanoate (1.18 g) and 2-propanol (12 mL) was stirred with heating with microwave irradiation at 150° C. for 7 hr. To the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (380 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-419631ff2f0249239f828c593ee2df88
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296746B2

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