Potassium Phosphate, Tribasic → HCID 58508759, compound

HRID 454777Notes

Reaction equation

HRID 454777 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:25]1[N:30]=[CH:29][C:28]([C:31]([NH:33][C:34]2[CH:46]=[C:45]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:44]=[CH:43][C:35]=2[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:32])=[CH:27][CH:26]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C1(C)C=CC=CC=1>[C:47]1([C:45]2[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:40])[CH3:41])=[O:37])=[C:34]([NH:33][C:31]([C:28]3[CH:29]=[N:30][C:25]([C:9]4[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=4)=[CH:26][CH:27]=3)=[O:32])[CH:46]=2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, Tribasic2×HCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine2×HCID 58508530HCID 58508530, compound

Product 1

HCID 58508759HCID 58508759, compoundYield 28.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst3×HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalyst3×HCID 1140TolueneSolvent

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine (48 mg), tripotassium phosphate (91 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.6 mg), and palladium(II) acetate (1.8 mg) were added to a toluene (1.6 mL) suspension of tert-butyl 2-(6-chloropyridine-3-carboxamido)-4-phenylbenzoate (80 mg), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (48 mg), tripotassium phosphate (91 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.6 mg), and palladium(II) acetate (1.8 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature, and then 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.6 mg) and palladium(II) acetate (1.8 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 2 hours. After cooling the reaction mixture to room temperature, the solvent was evaporated under reduced pressure, and chloroform and water were added to the residue. 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: 90-15% hexane/ethyl acetate] to obtain 25 mg of tert-butyl 4-phenyl-2-(6-(pyridin-4-yl)pyridine-3-carboxamido)benzoate as a light yellow solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours and 30 minutes
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 3 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. temperatureby heating
  7. temperatureto reflux under a nitrogen atmosphere for 2 hours
  8. temperatureAfter cooling the reaction mixture to room temperature
  9. customthe solvent was evaporated under reduced pressure, and chloroform and water
  10. additionwere added to the residue
  11. customThe insoluble substance was removed by filtration
  12. customThe organic layer was separated
  13. washwashed with a saturated aqueous solution of sodium chloride
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customthe solvent was evaporated under reduced pressure
  16. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-15% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-dc58f718b4c040598ae6eb0aa330c3d7
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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