Biphenyl → HCID 66851896, compound

HRID 880473Notes

Reaction equation

HRID 880473 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[N:30]1[CH2:31][CH2:32][N:27]([C:22]2[CH:21]=[C:20]([CH3:19])[CH:25]=[C:24]([CH3:26])[N:23]=2)[CH2:28][CH2:29]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7095BiphenylHCID 10796Cesium carbonateHCID 128819332-(Benzyloxy)-1-chloro-4-nitrobenzeneHCID 233680631-(4,6-Dimethylpyridin-2-YL)piperazine

Product 1

HCID 66851896HCID 66851896, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-benzyloxy-1-chloro-4-nitro-benzene (700 mg, 2.66 mmol), 1-(4,6-dimethyl-pyridin-2-yl)-piperazine (457 mg, 2.39 mmol) and caesium carbonate (2.58 g, 7.97 mmol) in toluene (30 mL) was purged with argon gas. Palladium acetate (24 mg, 0.106 mmol) and 2-(dicyclohexylphosphino)-2′-N,N-dimethylamino)-biphenyl (42 mg, 0.106 mmol) were added. After purging again with argon gas the reaction mixture was heated at reflux for 20 h. The reaction mixture was cooled, filtered and the filter cake was washed with ethyl acetate (30 mL). The combined filtrate and washings were washed successively with water (2×50 mL), brine (2×50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to yield a residue which was purified by flash column chromatography over silica gel (100-200 mesh) using 8-10% ethyl acetate in petroleum ether as eluent to afford 1-(2-benzyloxy-4-nitro-phenyl)-4-(4,6-dimethyl-2-pyridyl)piperazine (510 mg, 46%) as a pale yellow solid.

Workup

  1. customwas purged with argon gas
  2. customAfter purging again with argon gas the reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for 20 h
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. washthe filter cake was washed with ethyl acetate (30 mL)
  8. washThe combined filtrate and washings were washed successively with water (2×50 mL), brine (2×50 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto yield a residue which
  12. customwas purified by flash column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-8d5c1e3510ed4838bcdfb87ded8d4af0
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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