(E)-4-(6-methoxy-1-oxo-tetralin-2-yl)but-2-enal → 2-[[3-acetyl-1-[(3-chlorophenyl)methyl]-4H-pyridin-4-yl]methyl]-6-methoxy-tetralin-1-one

HRID 2207170Notes

Reaction equation

HRID 2207170 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH2:14]/[CH:15]=[CH:16]/[CH:17]=O)[CH2:7][CH2:6]2.[Cl:19][C:20]1[CH:21]=[C:22]([CH2:26][NH:27][CH:28]=[CH:29][C:30](=[O:32])[CH3:31])[CH:23]=[CH:24][CH:25]=1>>[C:30]([C:29]1[CH:15]([CH2:14][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]2=[O:13])[CH:16]=[CH:17][N:27]([CH2:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[CH:21]=2)[CH:28]=1)(=[O:32])[CH3:31]

Participants

3

Reactant 2

HCID 90303875(E)-4-(6-methoxy-1-oxo-tetralin-2-yl)but-2-enalHCID 1317358824-[(3-Chlorophenyl)methylamino]but-3-en-2-one

Product 1

HCID 1185580392-[[3-acetyl-1-[(3-chlorophenyl)methyl]-4H-pyridin-4-yl]methyl]-6-methoxy-tetralin-1-one

Procedure

The title compound 63 is prepared according to the procedure reported in step D of Example 8 with aldehyde 54 (100 mg, 0.41 mmol) and enamine 64 (90 mg, 0.42 mmol) as reactants. Purification by column chromatography on SiO2 (Petroleum Ether/EtOAc=2:1) afford the title compound 63 as a yellow solid. (Yield 70 mg, 39%).

Workup

  1. customThe title compound 63 is prepared
  2. customPurification by column chromatography on SiO2 (Petroleum Ether/EtOAc=2:1)

Sources & evidence

ORD record
ord-2d638abf508646b1a3657f1aca106e54
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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