Sodium Carbonate → N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-5-(4-pyridyl)thiophene-2-carboxamide

HRID 355745Notes

Reaction equation

HRID 355745 reaction equation
Br[C:2]1[S:6][C:5]([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:4][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:5]2[S:6][C:2]([C:28]3[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=3)=[CH:3][CH:4]=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 189406725-bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]thiophene-2-carboxamide

Product 1

HCID 22459274N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-5-(4-pyridyl)thiophene-2-carboxamideYield 65%

Reagents, catalysts & solvents 3

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

Procedure

5-bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]thiophene-2-carboxamide (0.31 g;0.76 mmol) was stirred with 4-pyridylboronic acid (0.093 g;0.76 mmol), tetrakis(triphenylphosphine)palladium(0) (0.045 g;5 mol %) and anhydrous sodium carbonate (0.089 g;0.84 mmol) in water (14 ml) and DME (14 ml) and the whole heated at reflux under Ar (18 hours). The reaction mixture was poured into 10% Na2CO3 (aq) (30 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 yellow, semi-solid residue which was triturated with acetone/Et2O. The solid that formed was collected by filtration and dried in vacuo to yield the tide compound as a yellow solid (0.2 g;65%), mp=191-194° 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 yellow, semi-solid residue which
  10. customwas triturated with acetone/Et2O
  11. customThe solid that formed
  12. filtrationwas collected by filtration
  13. customdried in vacuo

Sources & evidence

ORD record
ord-ef19e80929954cb98b1ea2c748c0e751
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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