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

HRID 355746Notes

Reaction equation

HRID 355746 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH:12]=2)=[O:9])=[CH:4][N:3]=1.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=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>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)=[N:3][CH:4]=2)=[O:9])=[CH:12][C:13]=1[N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1

Participants

7

Reactant 3

HCID 10340Sodium Carbonate2×HCID 2734379(Pyridin-4-yl)boronic acidHCID 189406772-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]pyridine-5-carboxamide

Product 1

HCID 18940667N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-2-(4-pyridyl)pyridine-5-carboxamide

Reagents, catalysts & solvents 3

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

Procedure

2-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]pyridine-5-carboxamide (0.125 g;0.31 mmol) was stirred with 4-pyridylboronic acid (0.038 g;0.31 mmol), tetrakis(triphenylphosphine)palladium(0) (0.024 g) and anhydrous sodium carbonate (0.036 g;0.34 mmol) in water (5 ml) and DME (5 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 5%MeOH/CHCl3 to yield a orange/yellow gum(0.060 g;48%).

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 5%MeOH/CHCl3
  9. customto yield a orange/yellow gum(0.060 g;48%)

Sources & evidence

ORD record
ord-ce126c1ffaba490dafeea661bffe246a
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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