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

HRID 1269610Notes

Reaction equation

HRID 1269610 reaction equation
[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH3:3].Br[CH2:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:25]([CH3:36])[CH:24]=1.C(N(CC)C(C)C)(C)C>CC#N>[CH3:36][C:25]1[CH:24]=[C:23]([CH2:22][N:4]([CH2:1][CH2:2][CH3:3])[C:5]2[CH:6]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=3)[CH:8]=[CH:9][CH:10]=2)[CH:35]=[CH:34][C:26]=1[O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18448426N-Propyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineHCID 58622841Ethyl [4-(bromomethyl)-2-methylphenoxy]acetate

Product 1

HCID 58622874Ethyl [2-methyl-4-({propyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetateYield 72.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-propyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (69.8 mg, 0.25 mmol) in anhydrous MeCN (6 mL) under nitrogen at room temperature, was added ethyl [4-(bromomethyl)-2-methylphenoxy]acetate (71.8 mg, 0.25 mmol) and N,N-diisopropyethylamine (43.5 μL, 0.25 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 (2×10 mL) and water (10 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification by SPE (5 g Silica cartridge eluted with 1:200 EtOAc:cyclohexane afforded the title compound as a colourless oil (88 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 SPE (5 g Silica cartridge
  6. washeluted with 1:200 EtOAc

Sources & evidence

ORD record
ord-04c8917ad3914422bdf55a7e5ffb95e7
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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