1-(2-Chloroethyl)-4-fluorobenzene → N-(1,1-Dimethylethyl)-3-[3-(4-fluorophenyl)propyl]-5-methyl-2-pyridine carboxamide

HRID 1030097

Reaktionsgleichung

Reaktionsgleichung von HRID 1030097
[CH3:1][C:2]([NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])[CH3:3].[CH2:15]([Li])CCC.[Br-].[Na+].[F:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Cl)=[CH:25][CH:24]=1>C1COCC1>[CH3:4][C:2]([NH:5][C:6]([C:8]1[C:13]([CH2:14][CH2:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([F:22])=[CH:24][CH:25]=2)=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=1)=[O:7])([CH3:1])[CH3:3]

Komponenten

6

Edukt 4

HCID 676221-(2-Chloroethyl)-4-fluorobenzeneHCID 253881Sodium BromideHCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamideHCID 178418339Butyllithium

Produkt 1

HCID 19821696N-(1,1-Dimethylethyl)-3-[3-(4-fluorophenyl)propyl]-5-methyl-2-pyridine carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Cool a solution of N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide in dry THF to -40° C. and add 2 equivalents of n-butyl lithium. Add a large excess of sodium bromide and stir for 15 minutes. Add 1 eq. of 4-fluorophenethyl chloride and stir for 2.5 hours while warming to -5° C. Quench the reaction with water and extract the product twice with ethyl acetate, then wash with brine (2X). Dry the organic phase over Na2SO4, filter and remove the solvent to produce the title compound.

Aufarbeitung

  1. stirringstir for 2.5 hours
  2. customQuench
  3. customthe reaction with water
  4. extractionextract the product twice with ethyl acetate
  5. washwash with brine (2X)
  6. dry with materialDry the organic phase over Na2SO4
  7. filtrationfilter
  8. customremove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-d52e31073cdd4be18443743cf47c3f6f
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104876

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