Diisopropylethylamine → Ethyl [4-({butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

HRID 1269606Notes

Reaction equation

HRID 1269606 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:26]([CH3:37])[CH:25]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:1]([N:5]([CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:26]([CH3:37])[CH:25]=1)[C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18448424N-Butyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineHCID 58622841Ethyl [4-(bromomethyl)-2-methylphenoxy]acetate

Product 1

HCID 58622862Ethyl [4-({butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetateYield 84.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-butyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (73 mg, 0.25 mmol) in anhydrous acetonitrile (5 mL) was added ethyl [4-(bromomethyl)-2-methylphenoxy]acetate (75 mg, 0.25 mmol) and N,N-diisopropylethylamine (43 μL, 0.25 mmol). The resulting solution was heated at reflux under nitrogen for 2 h and then cooled to room temperature. The solvent was removed in vacuo and the residue diluted with water (10 mL) and extracted with CH2Cl2 (30 mL). The organic extract was separated by hydrophobic frit and the solvent removed in vacuo. Purification by SPE (Silica, 5 g) eluting 99:1 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (105 mg).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux under nitrogen for 2 h
  3. customThe solvent was removed in vacuo
  4. additionthe residue diluted with water (10 mL)
  5. extractionextracted with CH2Cl2 (30 mL)
  6. extractionThe organic extract
  7. customwas separated by hydrophobic frit
  8. customthe solvent removed in vacuo
  9. customPurification by SPE (Silica, 5 g)
  10. washeluting 99:1 cyclohexane

Sources & evidence

ORD record
ord-1a349a58ed0643e29ad36d58d75a5a94
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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