Morpholine → 3-Methyl-1-(3-morpholino-2-pyridyl)pyrazole-4-carbaldehyde

HRID 1517578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517578
F[C:2]1[C:3]([N:8]2[CH:12]=[C:11]([CH:13]=[O:14])[C:10]([CH3:15])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>ClCCl>[CH3:15][C:10]1[C:11]([CH:13]=[O:14])=[CH:12][N:8]([C:3]2[C:2]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=1

Komponenten

4

Edukt 2

HCID 8083Morpholine2×HCID 582686081-(3-Fluoro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehyde

Produkt 1

HCID 582685493-Methyl-1-(3-morpholino-2-pyridyl)pyrazole-4-carbaldehydeAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 1-(3-fluoro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehyde (230 mg, 1.12 mmol) and morpholine (2 mL, 22.93 mmol) is heated under microwave irradiation (temperature 160° C., ramp time: 2 min, hold time: 10 min, potency: 250 W). The excess of morpholine is eliminated in vacuo and the residue is diluted in dichloromethane and washed in saturated aqueous solution of sodium bicarbonate. The organic layer is separated, dried over magnesium sulfate and the solvent evaporated in vacuo. The residue is purified by normal phase Isco chromatography using hexane/ethyl acetate as eluent (from 50 to 100% in ethyl acetate) to yield 72% of the title compound. MS (m/z): 273 (M+1).

Aufarbeitung

  1. washwashed in saturated aqueous solution of sodium bicarbonate
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent evaporated in vacuo
  5. customThe residue is purified by normal phase Isco chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e307915f2955461581b92132a96adc3d
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232289B2

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