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

HRID 341241

Reaktionsgleichung

Reaktionsgleichung von HRID 341241
[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 (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-bb050890774746689ad99ed63ecf81a4
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895745B2

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