Sodium t-butoxide → HCID 67776616, compound

HRID 1026228Notes

Reaction equation

HRID 1026228 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2Br)[NH2:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:17]=[C:18]3[C:19]([CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23]3)=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 23676156Sodium t-butoxideHCID 67778702HCID 67778702, compound

Product 1

HCID 67776616HCID 67776616, compoundYield 13.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-[4-(benzyloxy)phenyl]-1-(2-bromo-5-methoxybenzyl)hydrazine (1.50 g), palladium(II) acetate (41 mg), 1,1′-bis(diphenylphosphino)ferrocene (151 mg), sodium tert-butoxide (436 mg) and toluene (18 mL) was stirred under an argon atmosphere at 90° C. overnight. The solvent was evaporated under reduced pressure, and the obtained mixture was diluted with ethyl acetate and water, and the organic layer was separated. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (163 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe obtained mixture was diluted with ethyl acetate and water
  3. customthe organic layer was separated
  4. extractionThe separated aqueous layer was extracted again with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4ad72f52f7b149329f171b7a8e254f1f
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…