2,6-Difluorobenzaldehyde → ethyl 2-(2,6-difluorophenyl)-4-(pyridin-2-yl)-1H-imidazole-5-carboxylate

HRID 714929

Reaktionsgleichung

Reaktionsgleichung von HRID 714929
O[N:2]=[C:3]([C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])(=O)C.[NH4+:21].[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH:25]=O>C(O)(=O)C.CO>[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[C:25]1[NH:2][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:21]=1

Komponenten

6

Edukt 3

HCID 1362842,6-DifluorobenzaldehydeHCID 517165Ammonium AcetateHCID 178472895HCID 178472895, Verbindung

Produkt 1

HCID 59587497ethyl 2-(2,6-difluorophenyl)-4-(pyridin-2-yl)-1H-imidazole-5-carboxylateAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of ethyl 2-(hydroxyimino)-3-oxo-3-(pyridin-2-yl)propanoate (0.300 g, 1.4 mmol), ammonium acetate (0.104 g, 1.4 mmol) and 2,6-difluorobenzaldehyde (0.145 mL, 1.3 mmol) in acetic acid (6 mL) was heated in the microwave at 160° C. for 2 minutes. The reaction mixture was diluted with MeOH and purified by SPE using a MP-TsOH resin cartridge (2500 mg). The crude mixture obtained was purified by preparative HPLC to afford ethyl 2-(2,6-difluorophenyl)-4-(pyridin-2-yl)-1H-imidazole-5-carboxylate (0.029 g, 0.09 mmol, 7%) as a pale solid. LCMS (2) Rt: 2.46 min; m/z (ES+) 330.

Aufarbeitung

  1. custompurified by SPE
  2. customThe crude mixture obtained
  3. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ff96ec37b3dc4e8baf3423ead1d2c85e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187465B2

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