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

HRID 2207148노트

반응식

HRID 2207148 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 2734571Scandium(III) triflate촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a19f5583e4dc47209cfb00b26fa204bd
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376387B2

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