Sulfuric Acid → Ethyl 8-bromo-6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

HRID 931041

Reaktionsgleichung

Reaktionsgleichung von HRID 931041
[NH2:1][C:2]1[C:9]([Br:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Cl[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][O-].[K+].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[Br:10][C:9]1[C:2]2[N:3]([C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:1]=2)[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 14912506-Amino-5-bromopyridine-3-carbonitrileHCID 74089075Potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate

Produkt 1

HCID 118378872Ethyl 8-bromo-6-cyanoimidazo[1,2-a]pyridine-3-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 6-amino-5-bromonicotinonitrile (6.3 g), potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (15 g), sulfuric acid (2.2 mL) and ethanol (160 mL) was heated with reflux for 30 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 (4.3 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperaturewith reflux for 30 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2a2c8c3ab2aa495b82ba7df419346a5a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296746B2

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