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

HRID 355747
Notes
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Reaction equation

HRID 355747 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[CH:13]=2)=[O:10])[C:6]=1[O:7][CH3:8].[N:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=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>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:9]([C:5]2[C:6]([O:7][CH3:8])=[C:2]([C:30]3[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=3)[S:3][CH:4]=2)=[O:10])=[CH:13][C:14]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium Carbonate2×HCID 2734379(Pyridin-4-yl)boronic acidHCID 189406682-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-3-methoxythiophene-4-carboxamide

Product 1

HCID 22459332N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-2-(4-pyridyl)-3-methoxythiophene-4-carboxamide

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Bromo-N-[4-methoxy-3-(4-methyl- 1-piperazinyl)phenyl]-3-methoxythiophene-4-carboxamide (0.20 g;0.45 mmol) was stirred with 4-pyridylboronic acid (0.056 g;0.45 mmol), tetrakis(triphenylphosphine)palladium(0) (0.024 g) and anhydrous sodium carbonate (0.053 g;0.50 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 Na2SO4, 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 gum (0.088;44%).

Workup

  1. temperaturethe whole heated
  2. temperatureat reflux under Ar (18 hours)
  3. extractionextracted into CHCl3
  4. dry with materialdried over Na2SO4
  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 gum (0.088;44%)

Sources & evidence

ORD record
ord-d15e21b9974c4cc2a1ce18e1771982cd
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834471

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes