Water → Ethyl 2-(ethyl(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)phenyl)amino)acetate

HRID 709645Notes

Reaction equation

HRID 709645 reaction equation
[CH2:1]([N:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[N:30]=[C:29]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:28]([C:36]2[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=2[F:44])=[CH:27][CH:26]=1.O>CN(C=O)C>[CH2:1]([N:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:36]3[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=3[F:44])=[C:29]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[N:30]=2)[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18915234Ethyl 2-(ethyl(3-hydroxyphenyl)amino)acetateHCID 1177602646-(Bromomethyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine

Product 1

HCID 117760074Ethyl 2-(ethyl(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)phenyl)amino)acetateYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-(ethyl(3-hydroxyphenyl)amino)acetate (122 mg) in DMF (5.0 mL) were added potassium carbonate (75 mg) and 6-(bromomethyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine (100 mg), and the mixture was stirred at 80° C. for 1 hr. The mixture was allowed to cool to room temperature, and water was added. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (107 mg) as a colorless oil.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-16eb053042d745029675450ffce3ab5e
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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