Sodium Carbonate → N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-5-(4-pyridyl)furan-3-carboxamide

HRID 355744Notes

Reaction equation

HRID 355744 reaction equation
Br[C:2]1[O:6][CH:5]=[C:4]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH:11]=2)=[O:8])[CH:3]=1.[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7]([C:4]2[CH:3]=[C:2]([C:28]3[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=3)[O:6][CH:5]=2)=[O:8])=[CH:11][C:12]=1[N:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1

Participants

7

Reactant 3

HCID 10340Sodium Carbonate2×HCID 2734379(Pyridin-4-yl)boronic acidHCID 189406665-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]furan-3-carboxamide

Product 1

HCID 9930412N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-5-(4-pyridyl)furan-3-carboxamideYield 18%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

5-bromo-N-[4-methoxy-3-(4-methyl- 1-piperazinyl)phenyl]furan-3-carboxamide (0.16 g;0.41 mmol) was stirred with 4-pyridylboronic acid (0.050 g;0.41 mmol), tetrakis(triphenylphosphine)palladium(0) (0.024 g;5 mol %) and anhydrous sodium carbonate (0.047 g;0.45 mmol) in water (8 ml) and DME (8 ml) and the whole heated at reflux under Ar (18 hours). The reaction mixture was poured into 10% Na2CO3 (aq) (20 ml ) and extracted into CHCl3. The organic extracts were combined, dried over Na2 SO4, filtered and the filtrate evaporated in vacuo to a brown gum. The gum was purified by flash silica-gel chromatography and eluted with 4%MeOH/CHCl3 to yield a orange oil which was triturated with hexane/Et2O. The solid that formed was collected by filtration and dried in vacuo to yield the title compound as a tan solid (0.029 g;18%), mp=103°-105° C.

Workup

  1. temperaturethe whole heated
  2. temperatureat reflux under Ar (18 hours)
  3. extractionextracted into CHCl3
  4. customdried over Na2 SO4
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo to a brown gum
  7. customThe gum was purified by flash silica-gel chromatography
  8. washeluted with 4%MeOH/CHCl3
  9. customto yield a orange oil which
  10. customwas triturated with hexane/Et2O
  11. customThe solid that formed
  12. filtrationwas collected by filtration
  13. customdried in vacuo

Sources & evidence

ORD record
ord-22539d91e90648ebbb0dcd603c0b3154
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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