Potassium Fluoride → HCID 67153538, compound

HRID 1160925Notes

Reaction equation

HRID 1160925 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:20][C:21]2[CH:22]=[N:23][C:24](Cl)=[C:25]([CH3:27])[CH:26]=2)[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[F-].[K+].[F:33][C:34]([F:46])([F:45])[O:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:20][C:21]2[CH:22]=[N:23][C:24]([C:39]3[CH:38]=[CH:37][C:36]([O:35][C:34]([F:33])([F:45])[F:46])=[CH:41][CH:40]=3)=[C:25]([CH3:27])[CH:26]=2)[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 86615990HCID 86615990, compound

Product 1

HCID 67153538HCID 67153538, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-{4-[1-(6-Chloro-5-methyl-pyridin-3-yloxy)-3,3-dimethyl-butyl]-benzoylamino}-propionic acid methyl ester (200 mg, 0.46 mmol), potassium fluoride (80 mg, 1.38 mmol), 4-trifluoromethoxyphenyl boronic acid (190 mg, 0.92 mmol) and tetrakis(triphenylphosphine)palladium (53 mg, 0.046 mmol) are placed in a flask. After the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml) is added. The resulting solution is refluxed overnight, loaded on silica gel, eluted with hexane and ethyl acetate to give the titled compound (220 mg).

Workup

  1. customAfter the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml)
  2. additionis added
  3. temperatureThe resulting solution is refluxed overnight
  4. washeluted with hexane and ethyl acetate

Sources & evidence

ORD record
ord-123f1b352e6e476a96f571134ef0bce4
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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