Ethyl Acetate → HCID 117760248, compound

HRID 709715Notes

Reaction equation

HRID 709715 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:6]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[CH:5][CH:4]=1.[OH:23][C:24]1[C:25]([O:36][CH3:37])=[C:26]([CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:27]=[CH:28][CH:29]=1.[C:38](=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C(#N)C>[CH3:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:7]1[N:8]=[C:3]([CH2:2][O:23][C:24]2[C:25]([O:36][CH3:37])=[C:26]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:38])=[O:33])[CH:27]=[CH:28][CH:29]=2)[CH:4]=[CH:5][C:6]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[F:22]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 117759835HCID 117759835, compoundHCID 1177599996-(Chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine

Product 1

HCID 117760248HCID 117760248, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-(chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine (300 mg) in acetonitrile (10 mL) were added methyl 3-(3-hydroxy-2-methoxyphenyl)propanoate (210 mg) and cesium carbonate (512 mg), and the mixture was heated under reflux for 15 hr. Ethyl acetate was added to the reaction mixture, and the insoluble material was filtered off. The solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (450 mg) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hr
  3. filtrationthe insoluble material was filtered off
  4. customThe solvent in the filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-654971f1dbce44ad9fdafdfe520af978
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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