Citric Acid → Tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoate

HRID 454775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454775
[C:1]1(OB=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([NH:27][C:28]2[CH:40]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:38]=[CH:37][C:29]=2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26])[CH:20]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:41]1([C:39]2[CH:38]=[CH:37][C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[C:28]([NH:27][C:25]([C:21]3[CH:20]=[C:19]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:24]=[CH:23][N:22]=3)=[O:26])[CH:40]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

9

Edukt 4

HCID 311Citric AcidHCID 62657Potassium Phosphate, Tribasic2×HCID 14438906HCID 14438906, Verbindung2×HCID 58508497Tert-butyl 2-(4-chloropyridine-2-carboxamido)-4-phenylbenzoate

Produkt 1

HCID 58508724Tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoateAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysator2×HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysator2×HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Phenylboranic acid (21 mg), tripotassium phosphate (69 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.2 mg), and palladium(II) acetate (1.3 mg) were added to a toluene (1.2 mL) solution of tert-butyl 2-(4-chloropyridine-2-carboxamido)-4-phenylbenzoate (60 mg), followed by heating to reflux under a nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature, and then phenylboranic acid (5.4 mg), tripotassium phosphate (16 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.2 mg), and palladium(II) acetate (1.3 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and a 10% aqueous solution of citric acid were added thereto. The insoluble substance was removed by filtration. 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 [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-85% hexane/ethyl acetate] to obtain 65 mg of tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoate as a colorless oily substance.

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 3 hours
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 2 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe insoluble substance was removed by filtration
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-85% hexane/ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-bdee635596ce46458cb31fce7ad13748
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492582B2

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