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

HRID 1269615Notes

Reaction equation

HRID 1269615 reaction equation
[CH2:1]([NH:5][C:6]1[C:7]([CH3:22])=[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[CH2:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:27]([CH3:38])[CH:26]=1.C(N(CC)C(C)C)(C)C>CC#N>[CH2:1]([N:5]([CH2:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:27]([CH3:38])[CH:26]=1)[C:6]1[C:7]([CH3:22])=[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 18448423N-Butyl-N-[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineHCID 58622841Ethyl [4-(bromomethyl)-2-methylphenoxy]acetate

Product 1

HCID 58622849Ethyl [4-({butyl[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetateYield 64.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-butyl-N-[2-methyl-4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (102 mg, 0.33 mmol) in anhydrous MeCN (8 mL) under nitrogen at room temperature was added ethyl [4-(bromomethyl)-2-methylphenoxy]acetate (95.3 mg, 0.33 mmol) and N,N-diisopropyethylamine (57.8 μL, 0.33 mmol). The resultant solution was heated to reflux and stirred for 3 h. The reaction mixture was allowed to cool to room temperature and the solvent was removed in vacuo. The residue was partitioned between CHCl3 (2×10 mL) and water (10 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification by Biotage™ chromatography (40 g Silica column) eluted with 1:99–1:49 EtOAc:cyclohexane afforded the title compound as a colourless oil (110 mg).

Workup

  1. temperatureto reflux
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between CHCl3 (2×10 mL) and water (10 mL)
  4. customthe solvent was removed in vacuo
  5. customPurification by Biotage™ chromatography (40 g Silica column)
  6. washeluted with 1:99–1:49 EtOAc

Sources & evidence

ORD record
ord-649609dd8fcb4aca9de82d7e86fb957a
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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