Potassium Carbonate → HCID 68814938, compound

HRID 732537Notes

Reaction equation

HRID 732537 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15](I)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:16]=[C:15]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[F:19])[CH:14]=[C:6]([C:7](=[O:8])[N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])[CH:5]=1)=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 21086185Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

Product 1

HCID 68814938HCID 68814938, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Add 1,4-dioxane (10 mL), 5-iodo-N-methyl-N-propyl-isophthalamic acid methyl ester (0.720 g, 2.00 mmol), 2-fluorophenylboronic acid (0.364 g, 2.60 mmol), tetrakis(triphenylphosphine)palladium (0) (0.347 g, 0.300 mmol), and potassium carbonate (0.829 g, 6.00 mmol) to a sealed flask flushed with nitrogen. Heat the mixture overnight and cool to room temperature. Filter the mixture though a filtering agent, concentrate and purify (silica gel chromatography, eluting with 4:96 ethyl acetate:hexanes) to give the title compound (0.297 g, 45%).

Workup

  1. customflushed with nitrogen
  2. temperatureHeat the mixture overnight
  3. filtrationFilter the mixture though a filtering agent
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 4:96 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-e9e2cdaa19a84bada553cf5360a6a1fd
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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