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

HRID 535680

반응식

HRID 535680 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-e8ee74b43f8e49dc9f0fc656bba9c955
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859534B2

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