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

HRID 2207148Notes

Reaction equation

HRID 2207148 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 118557876N-[2-(3-acetyl-1-benzyl-4H-pyridin-4-yl)ethyl]-3,4-dimethoxy-N-phenyl-benzamideYield 58.4%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-a19f5583e4dc47209cfb00b26fa204bd
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

Loading…