Potassium Fluoride → HCID 67488146, compound

HRID 251313Notes

Reaction equation

HRID 251313 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][NH:6][C:7](=[O:27])[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[CH:19][C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[C:29]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30].[F-].[K+]>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:28])[CH2:4][CH2:5][NH:6][C:7](=[O:27])[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([C:36]3[CH:37]=[CH:38][C:33]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:34][CH:35]=3)=[CH:22][CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27343204-tert-Butylphenylboronic acidHCID 67485994HCID 67485994, compound

Product 1

HCID 67488146HCID 67488146, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-{4-[1-(4-bromo-benzylidene)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester (2.6 g, 5.86 mmol), 4-t-butyl phenyl boronic acid (2.08 g, 12 mmol), potassium fluoride (1.02 g, 17.6 mmol) and tetrakis(triphenylphosphine)palladium (0.677 g, 0.59 mmol) are placed in a flask. The system is purged with nitrogen. Toluene (40 mL) and water (10 ml) are added and the resulting mixture is refluxed overnight. The reaction is loaded directly onto silica gel and chromatographed using EtOAc/hexanes to yield the titled compound as a yellow oil (0.95 g).

Workup

  1. customThe system is purged with nitrogen
  2. additionToluene (40 mL) and water (10 ml) are added
  3. temperaturethe resulting mixture is refluxed overnight
  4. customchromatographed

Sources & evidence

ORD record
ord-ac79e6fdc9004d2cb4c4d726d086f6b5
Source dataset
uspto-grants-2011_01
Patent number
US07863329B2

Reaction notes

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