Sodium Carbonate → Tert-butyl 4-phenyl-2-(5-phenylpyridine-2-carboxamido)benzoate

HRID 454766Notes

Reaction equation

HRID 454766 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1(OB=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:17]1[CH:18]=[CH:19][C:20]([C:23]([NH:25][C:26]2[CH:38]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:36]=[CH:35][C:27]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C.COCCOC>[C:39]1([C:37]2[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[C:26]([NH:25][C:23]([C:20]3[CH:19]=[CH:18][C:17]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[CH:22][N:21]=3)=[O:24])[CH:38]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

8

Reactant 3

HCID 10340Sodium Carbonate2×HCID 14438906HCID 14438906, compound2×HCID 58508787Tert-butyl 2-(5-bromopyridine-2-carboxamido)-4-phenylbenzoate

Product 1

HCID 58508956Tert-butyl 4-phenyl-2-(5-phenylpyridine-2-carboxamido)benzoateYield 92.2%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium carbonate (55 mg), phenylboranic acid (38 mg), water (0.35 mL), and bis(triphenylphosphine)palladium(II) dichloride (3.7 mg) were added to an ethylene glycol dimethyl ether (1.2 mL) suspension of tert-butyl 2-(5-bromopyridine-2-carboxamido)-4-phenylbenzoate (0.12 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and then sodium carbonate (55 mg), phenylboranic acid (38 mg), and bis(triphenylphosphine)palladium(II) dichloride (3.7 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 ethyl acetate and water 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: 90-80% hexane/ethyl acetate] to obtain 0.11 g of tert-butyl 4-phenyl-2-(5-phenylpyridine-2-carboxamido)benzoate as a white solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 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: 90-80% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-04e95ca3093246b7a74c34e36d2c65d7
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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