Dimethylformamide → Methyl 2-(4-formyl-3-methyl-pyrazol-1-yl)pyridine-3-carboxylate

HRID 1517569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517569
[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1.CN(C)C=O>O>[CH:7]([C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:16]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:5]=1)=[O:8]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 242724Methyl 2-fluoronicotinateHCID 1784345503-methyl-1H-pyrazole-4-carbaldehyde

Produkt 1

HCID 86653542Methyl 2-(4-formyl-3-methyl-pyrazol-1-yl)pyridine-3-carboxylateAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 3-methyl-1H-pyrazole-4-carbaldehyde (300 mg, 2.72 mmol), potassium carbonate (565 mg, 4.08 mmol), methyl 2-fluoropyridine-3-carboxylate (507 mg, 3.27 mmol) and dimethylformamide (2 mL) is stirred at 60° C. for 16 h. Water is added and the compound is extracted in ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate and solvent is evaporated. The crude mixture is purified by normal phase Isco chromatography using hexane:ethyl acetate, 2:1 as eluent to yield 422 mg of the title compound. MS (m/z): 246 (M+1).

Aufarbeitung

  1. extractionthe compound is extracted in ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate and solvent
  4. customis evaporated
  5. customThe crude mixture is purified by normal phase Isco chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f549775b1fe94cf1b2f647957482649a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232289B2

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