Citric Acid → HCID 58508948, compound

HRID 454780Notes

Reaction equation

HRID 454780 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Br[C:49]1[CH:61]=[CH:60][C:52]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[C:51]([NH:62][C:63]([C:65]2[CH:66]=[N:67][CH:68]=[C:69]([C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[CH:70]=2)=[O:64])[CH:50]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>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].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[NH:7]([C:49]1[CH:61]=[CH:60][C:52]([C:53]([O:55][C:56]([CH3:58])([CH3:57])[CH3:59])=[O:54])=[C:51]([NH:62][C:63]([C:65]2[CH:66]=[N:67][CH:68]=[C:69]([C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[CH:70]=2)=[O:64])[CH:50]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

10

Reactant 5

HCID 311Citric AcidHCID 6115AnilineHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58508430Tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate

Product 1

HCID 58508948HCID 58508948, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (0.14 g), aniline (0.030 mL), tris(dibenzylideneacetone)dipalladium(0) (2 mg), palladium(II) acetate (1 mg), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (5 mg) were added to a toluene (2.5 mL) solution of tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (0.10 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 10 minutes. The reaction mixture was cooled to room temperature, and then ethyl acetate and a 10% aqueous solution of citric acid were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 91-80% hexane/ethyl acetate] to obtain tert-butyl 4-anilino-2-(5-phenylpyridine-3-carboxamido)benzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour and 10 minutes
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 91-80% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-52047f9fdc604f7e9d40c30e06dc61c4
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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