4-Ethyl-2-methylpyridine → HCID 178436305, Verbindung

HRID 1827461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827461
C([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1)C.[CH2:10]([Li])[CH2:11]CC.[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH:25]=[O:26])=[N:21][NH:22]2)=[CH:18][CH:17]=1>C1COCC1>[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH:25]([OH:26])[CH2:9][C:5]3[CH:4]=[CH:3][C:8]([CH2:10][CH3:11])=[CH:7][N:6]=3)=[N:21][NH:22]2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 683074-Ethyl-2-methylpyridineHCID 178418339ButyllithiumHCID 178520036HCID 178520036, Verbindung

Produkt 1

HCID 178436305HCID 178436305, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-ethyl-2-methylpyridine (0.458 9, 3.79 mmol) in THF (4mL) at −50 degrees Celsius, add butyl lithium (1.5 mL, 2.5 M, 3.79 mmol) slowly and stir for 10 minutes. To the reaction, slowly add a solution of 6-Chloro-1H-indazole-3-carbaldehyde (0.5 g, 1.89 mmol) in THF (4 mL). After stirring for 10 minutes, the reaction was quenched with 1 N citric acid (10 mL). The mixture was diluted with EtOAc (50 mL), water (20 mL), and saturated NaCl (10 mL). The layers were separated, and the aqueous was extracted with EtOAc (3×15 mL). The organics were combined and washed with saturated NaCl (20 mL). After drying the organic layer over Na2SO4, the solids were removed by filtration and the liquid was concentrated to an oil by rotary evaporation. Chromatography (40 g silica gel, 60–100% EtOAc/hex) yields the desired product (142 mg, 32%) and recovered 6-Chloro-1H-indazole-3-carbaldehyde (348 mg).

Aufarbeitung

  1. customTo the reaction
  2. stirringAfter stirring for 10 minutes
  3. customthe reaction was quenched with 1 N citric acid (10 mL)
  4. additionThe mixture was diluted with EtOAc (50 mL), water (20 mL), and saturated NaCl (10 mL)
  5. customThe layers were separated
  6. extractionthe aqueous was extracted with EtOAc (3×15 mL)
  7. washwashed with saturated NaCl (20 mL)
  8. dry with materialAfter drying the organic layer over Na2SO4
  9. customthe solids were removed by filtration
  10. concentrationthe liquid was concentrated to an oil by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-1cf3762e7edb43eba9e8b60d8675ebcc
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053107B2

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