Piperazine, 2-pyridylethyl- → 5-Methoxy-N,N-dimethyl-7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxamide

HRID 535680Notes

Reaction equation

HRID 535680 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:7][C:6]=2[CH:5]=[C:4]([O:16][CH3:17])[CH:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[CH3:17][O:16][C:4]1[CH:3]=[C:2]([N:29]2[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=3)[CH2:27][CH2:28]2)[C:10]2[O:9][C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:7][C:6]=2[CH:5]=1

Participants

8

Reactant 4

HCID 566605Piperazine, 2-pyridylethyl-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 596367447-Bromo-5-methoxy-N,N-dimethylbenzofuran-2-carboxamide

Product 1

HCID 596367115-Methoxy-N,N-dimethyl-7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxamide

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Bromo-5-methoxy-N,N-dimethylbenzofuran-2-carboxamide (0.20 g, 0.67 mmol), 1-(2-pyridin-2-yl-ethyl)piperazine (0.13 g, 0.67 mmol), Pd2 dba3 (0.031 g, 0.030 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (0.032 g, 0.070 mmol) and sodium t-butoxide (0.14 g, 1.41 mmol) were heated in toluene (1 mL) at 100° C. for 2 h. The mixture was allowed to cool. Ethyl acetate was added and the mixture was filtered through a pad of celite. The filtrate was washed with water and brine, dried over MgSO4 and the solvent was removed by rotary evaporation. The crude product was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-3%) to give the title compound. Yield: 0.14 g (52%).

Workup

  1. temperatureto cool
  2. filtrationthe mixture was filtered through a pad of celite
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed by rotary evaporation
  6. customThe crude product was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-3%)

Sources & evidence

ORD record
ord-e8ee74b43f8e49dc9f0fc656bba9c955
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Reaction notes

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