Diisopropylethylamine → Methyl [2-methyl-4-({[2-(methylthio)ethyl][4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate

HRID 1269611Notes

Reaction equation

HRID 1269611 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][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.Br[CH2:23][C:24]1[CH:35]=[CH:34][C:27]([O:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:26]([CH3:36])[CH:25]=1.C(N(CC)C(C)C)(C)C>CC#N>[CH3:36][C:26]1[CH:25]=[C:24]([CH2:23][N:5]([CH2:4][CH2:3][S:2][CH3:1])[C:6]2[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH:35]=[CH:34][C:27]=1[O:28][CH2:29][C:30]([O:32][CH3:33])=[O:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18448420N-[2-(Methylthio)ethyl]-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineHCID 85903007Methyl [4-(bromomethyl)-2-methylphenoxy]acetate

Product 1

HCID 58622870Methyl [2-methyl-4-({[2-(methylthio)ethyl][4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetateYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-[2-(methylthio)ethyl]-N-[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (0.27 g, 0.864 mmol) in anhydrous MeCN (22 mL) under nitrogen at room temperature was added methyl [4-(bromomethyl)-2-methylphenoxy]acetate (0.248 g, 0.864 mmol) and N,N-diisopropyethylamine (0.15 mL, 0.864 mmol). The resultant mixture 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 (2×30 mL) and water (30 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification by SPE (20 g Silica cartridge), eluted with 1:99–1:33 EtOAc:cyclohexane afforded the title compound as a yellow oil (249 mg).

Workup

  1. temperatureto reflux
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between CHCl3 (2×30 mL) and water (30 mL)
  4. customthe solvent was removed in vacuo
  5. customPurification by SPE (20 g Silica cartridge)
  6. washeluted with 1:99–1:33 EtOAc

Sources & evidence

ORD record
ord-28b86d39cb2b4ba3bea324583233c822
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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