Water → HCID 68711230, compound

HRID 2376274Notes

Reaction equation

HRID 2376274 reaction equation
Br[C:2]1[C:3]([CH3:22])=[C:4]([CH3:21])[C:5]2[O:9][CH2:8][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=3)[C:6]=2[C:19]=1[CH3:20].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(C)([O-])C.[Na+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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>[CH2:23]([NH:30][C:2]1[C:3]([CH3:22])=[C:4]([CH3:21])[C:5]2[O:9][CH2:8][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=3)[C:6]=2[C:19]=1[CH3:20])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 23114095HCID 23114095, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 68711230HCID 68711230, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran obtained in Reference Example 18 (920 mg, 2.56 mmol) and benzylamine (0.34 mL, 3.07 mmol) in toluene (10 mL), were added palladium acetate (6 mg, 0.03 mmol) and BINAP (48 mg, 0.09 mmol) at room temperature, and the mixture was stirred under argon stream for 15 minutes. Sodium tert-butoxide (344 mg, 3.58 mmol) was added to the reaction solution at room temperature, and then the mixture was heated under reflux for 18 hours. Water was added to the reaction solution, which was extracted with ethyl acetate, the organic layer was washed with water and a saturated brine and then was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain 900 mg (yield 91%) of the title compound as an oily matter. Oily matter.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. extractionwas extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materiala saturated brine and then was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-b674a591f841478f9fb09046b4f9abb2
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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