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

HRID 1030097

Reaction equation

HRID 1030097 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d52e31073cdd4be18443743cf47c3f6f
Source dataset
uspto-grants-1992_04
Patent number
US05104876

Linked notes

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