Sodium Sulfate → N-[2-(3-acetyl-1-benzyl-4H-pyridin-4-yl)ethyl]-3,4-dimethoxy-N-phenyl-benzamide

HRID 2207148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207148
[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:8]([NH:15][CH:16]=[CH:17][C:18](=[O:20])[CH3:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:41]=[CH:42][C:43]=1[O:44][CH3:45])[C:26]([N:28]([CH2:35][CH2:36]/[CH:37]=[CH:38]/[CH:39]=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[C:18]([C:17]1[CH:37]([CH2:36][CH2:35][N:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:26](=[O:27])[C:25]2[CH:41]=[CH:42][C:43]([O:44][CH3:45])=[C:23]([O:22][CH3:21])[CH:24]=2)[CH:38]=[CH:39][N:15]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=1)(=[O:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 24436Sodium SulfateHCID 5214434-(Benzylamino)but-3-en-2-oneHCID 1185578373,4-dimethoxy-N-[(E)-5-oxopent-3-enyl]-N-phenyl-benzamide

Produkt 1

HCID 118557876N-[2-(3-acetyl-1-benzyl-4H-pyridin-4-yl)ethyl]-3,4-dimethoxy-N-phenyl-benzamideAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734571Scandium(III) triflateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of Sc(OTf)3 (10% mol), Na2SO4 (3 equiv) in dry CH2Cl2 (15 mL) is added a solution of enamine 30 (332 mg, 1.9 mmol) and enal 35 (644 mg, 1.9 mmol) in dry CH2Cl2 (5 mL). The reaction mixture was stirred at room temperature for 48 h. The reaction solution is filtered on Celite and the solvent removed under pressure. The residue obtained is purified on SiO2 (gradient of EtOAc in Petroleum ether) to afford the title compound 32 as a yellow oil (Yield 551 mg, 58%).

Aufarbeitung

  1. filtrationThe reaction solution is filtered on Celite
  2. customthe solvent removed under pressure
  3. customThe residue obtained
  4. customis purified on SiO2 (gradient of EtOAc in Petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-a19f5583e4dc47209cfb00b26fa204bd
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376387B2

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