Sulfuric Acid → Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

HRID 405784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405784
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[K].Cl[C:11](=[CH:17]O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)O>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][N:8]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 706222-Amino-5-bromopyridineHCID 86677443Ethyl 2-chloro-3-hydroxyacrylate potassium salt

Produkt 1

HCID 22031055Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

To a stirring suspension of 5-bromopyridin-2-amine (1.2 g, 7.05 mmol) and ethyl 2-chloro-3-hydroxyacrylate potassium salt (6.6 g, 28.19 mmol) (prepared in a similar manner as 22) in EtOH (100 mL) at room temperature was added sulfuric acid (751 μL, 14.10 mmol) dropwise. The reaction mixture was heated at 78° C. overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the pH was adjusted between 6-8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic was washed with brine and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography to yield ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate (24s). MS m/z 270.2 (M+1)+.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationthe solvent was concentrated
  3. extractionThe crude product was extracted with ethyl acetate
  4. washThe organic was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe crude product was purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-86420139cbc04ae9b7acb9cc6abe8afd
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754071B2

Notizen zur Reaktion

Wird geladen…