Potassium Carbonate → Ethyl 6-(5'-chloro-2'-{[(4-fluorophenyl)methyl]oxy}2-biphenylyl)-2-pyridinecarboxylate

HRID 269571Notes

Reaction equation

HRID 269571 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:37][C:36]2[CH:39]=[CH:40][C:33]([F:32])=[CH:34][CH:35]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 136335797Ethyl 6-(5'-chloro-2'-hydroxy-2-biphenylyl)-2-pyridinecarboxylate

Product 1

HCID 58730992Ethyl 6-(5'-chloro-2'-{[(4-fluorophenyl)methyl]oxy}2-biphenylyl)-2-pyridinecarboxylateYield 82.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 6-(5′-chloro-2′-hydroxy-2-biphenylyl)-2-pyridinecarboxylate (177 mg, 0.5 mmol), potassium carbonate (138 mg, 1 mmol) and 4-fluorobenzyl bromide (104 mg, 0.55 mmol) in acetone (4 ml) was stirred and refluxed for 2 hours then cooled, filtered, evaporated and chromatographed on silica eluting with ethyl acetate/iso-hexane (1:9) to give 190 mg of white solid. LC/MS t=3.79, [MH+] 462.3

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturethen cooled
  3. filtrationfiltered
  4. customevaporated
  5. customchromatographed on silica eluting with ethyl acetate/iso-hexane (1:9)

Sources & evidence

ORD record
ord-d58ea619476b4d63811a3e8d7affc9b2
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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