Ethanol → HCID 21875914, compound

HRID 858500Notes

Reaction equation

HRID 858500 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([Cl:12])=[CH:4][C:3]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=O.CCO>CCOC(C)=O>[Cl:12][C:5]1[C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]2[N:1]=[C:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=3)[N:13]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=3)[C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 142732-PyridinecarboxaldehydeHCID 21875983HCID 21875983, compound

Product 1

HCID 21875914HCID 21875914, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-{[2-amino-5-chloro-4-(trifluoromethyl)phenyl]amino}phenyl)ethanol (1.83 g, 5.54 mmol), 2-pyridinecarboxaldehyde (0.53 ml, 5.54 mmol), and EtOH (40 ml) was refluxed for 1 hour. After cooling to room temperature, the solvent was removed. The residue was dissolved with benzene (50 ml) and treated with Pb(OAc)4 (3.38 g, 6.10 mmol) at room temperature for 1 hour. The mixture was diluted with EtOAc and the solution was washed with sat. NaHCO3 aq. and brine. The organic fraction was dried over MgSO4, then filtered. After evaporation in vacuo, the residue was purified by silica-gel column chromatography eluting with hexane/EtOAc=5/2 to afford 1.20 g (52%) of the title compound.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved with benzene (50 ml)
  4. washthe solution was washed with sat. NaHCO3 aq. and brine
  5. dry with materialThe organic fraction was dried over MgSO4
  6. filtrationfiltered
  7. customAfter evaporation in vacuo
  8. customthe residue was purified by silica-gel column chromatography
  9. washeluting with hexane/EtOAc=5/2

Sources & evidence

ORD record
ord-20ef70791c7e49a689b0b13583ac26e0
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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