Benzylamine → HCID 66759427, compound

HRID 1850376Notes

Reaction equation

HRID 1850376 reaction equation
CC(C)([O-])C.[Na+].Br[C:8]1[C:9]([CH3:21])=[C:10]([CH3:20])[C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2[CH:19]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH2:22]([NH:29][C:8]1[C:9]([CH3:21])=[C:10]([CH3:20])[C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2[CH:19]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

9

Reactant 4

HCID 7504BenzylamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 667597135-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one

Product 1

HCID 66759427HCID 66759427, compoundYield 67%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium t-butoxide (13.9 g, 145 mmol) was added to a mixture of toluene (100 mL) containing 5-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (12.8 g, 48.2 mmol) synthesized in Reference Example 18, benzylamine (15.5 g, 145 mmol), palladium acetate (541 mg, 2.41 mmol) and BINAP (4.50 g, 7.23 mmol), and the mixture was stirred under heated reflux for 20 hours. After cooled to room temperature, water was added to the reaction solution, and extraction was performed using ethyl acetate. The organic layer was washed with saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 100:0 to 50:50) to give 9.48 g of the title compound (yield: 67%).

Workup

  1. temperatureunder heated
  2. temperaturereflux for 20 hours
  3. washThe organic layer was washed with saturated saline
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 100:0 to 50:50)

Sources & evidence

ORD record
ord-d16fd744b3194be7890ef5035fec9cd9
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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