Benzaldehyde → Tert-butyl 4-(2-(benzylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate

HRID 454751Notes

Reaction equation

HRID 454751 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[C:32]([NH:43][C:44]([C:46]2[CH:47]=[N:48][CH:49]=[C:50]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH:51]=2)=[O:45])[CH:31]=1>O.C(Cl)(Cl)Cl.C(Cl)Cl.C(O)(=O)C>[CH2:1]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[C:32]([NH:43][C:44]([C:46]2[CH:47]=[N:48][CH:49]=[C:50]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[CH:51]=2)=[O:45])[CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 240Benzaldehyde2×HCID 5049666Sodium triacetoxyborohydride4×HCID 58508762Tert-butyl 4-(2-aminophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate

Product 1

HCID 66990930Tert-butyl 4-(2-(benzylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent3×

Procedure

Benzaldehyde (0.027 mL) and sodium triacetoxyborohydride (70 mg) were added to a methylene chloride (1 mL) suspension of tert-butyl 4-(2-aminophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate (0.10 g) at room temperature, followed by stirring at the same temperature for 3 hours and 30 minutes. Methylene chloride (2 mL) was added to the reaction mixture at room temperature, followed by stirring at the same temperature for 1 hour and 50 minutes. Acetic acid (0.013 mL) and sodium triacetoxyborohydride (47 mg) were added to the reaction mixture at room temperature, followed by stirring at the same temperature for 2 hours and 50 minutes. Sodium triacetoxyborohydride (47 mg), methylene chloride (3 mL), and benzaldehyde (0.027 mL) were added to the reaction mixture at room temperature, followed by heating to reflux for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then sodium triacetoxyborohydride (47 mg) was added thereto, followed by heating to reflux for 4 hours and 40 minutes. The reaction mixture was cooled to room temperature, and then chloroform and water were added thereto. The organic layer was separated 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:85-60% hexane/ethyl acetate] to obtain 78 mg of tert-butyl 4-(2-(benzylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate as a light yellow solid.

Workup

  1. stirringby stirring at the same temperature for 1 hour and 50 minutes
  2. stirringby stirring at the same temperature for 2 hours and 50 minutes
  3. temperatureby heating
  4. temperatureto reflux for 1 hour and 30 minutes
  5. temperatureby heating
  6. temperatureto reflux for 4 hours and 40 minutes
  7. temperatureThe reaction mixture was cooled to room temperature
  8. customThe organic layer was separated
  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 [eluent:85-60% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-d08fb14c3812417b8f407c58b072b471
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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