Chloroacetaldehyde → Methyl imidazo(1,2-a)pyridine-7-carboxylate

HRID 536293

Reaktionsgleichung

Reaktionsgleichung von HRID 536293
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].Cl[CH2:18][CH:19]=O>CCO>[N:1]1[CH:18]=[CH:19][N:3]2[CH:4]=[CH:5][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:2]=12

Komponenten

5

Edukt 3

HCID 33ChloroacetaldehydeHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 15096964Methyl imidazo(1,2-a)pyridine-7-carboxylateAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of Methyl 2-aminopyridine-4-carboxylate (10.0 g, 66 mmol, 1.0 equiv) in EtOH (150 ml) was added NaHCO3 (11.1 g, 132 mmol, 2.0 equiv) followed by chloroacetaldehyde (50% by weight in water, 13.0 ml, 99 mmol, 1.5 equiv). The mixture was refluxed for 2 h. Solvents were removed under reduced pressure and the crude mixture was partitioned between water and EtOAc. The resulting precipitate was washed with Et2O and recrystallised from MeOH/Et2O to afford 8.4 g of product. 1H NMR (400 MHz, DMSO-d6): 8.66 (1H, d), 8.16 (2H, s), 7.80 (1H, s), 7.33 (1H, d), 3.90 (3H, s). MS: [M+H]+ 177.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 h
  2. customSolvents were removed under reduced pressure
  3. customthe crude mixture was partitioned between water and EtOAc
  4. washThe resulting precipitate was washed with Et2O
  5. customrecrystallised from MeOH/Et2O

Quellen und Nachweise

ORD-Eintrag
ord-ebf79aa719ee48b1808f6a8112475117
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859583B2

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