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

HRID 2207172Notes

Reaction equation

HRID 2207172 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.[F:19][C:20]([F:35])([F:34])[C:21]1[CH:22]=[C:23]([CH2:27][NH:28][CH:29]=[CH:30][C:31](=[O:33])[CH3:32])[CH:24]=[CH:25][CH:26]=1>>[C:31]([C:30]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:28]([CH2:27][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:34])([F:35])[F:19])[CH:22]=2)[CH:29]=1)(=[O:33])[CH3:32]

Participants

3

Reactant 2

HCID 90303875(E)-4-(6-methoxy-1-oxo-tetralin-2-yl)but-2-enalHCID 1317358834-[[3-(Trifluoromethyl)phenyl]methylamino]but-3-en-2-one

Product 1

HCID 1185578712-[[3-acetyl-1-[[3-(trifluoromethyl)phenyl]methyl]-4H-pyridin-4-yl]methyl]-6-methoxy-tetralin-1-one

Procedure

The title compound 65 is prepared according to the procedure reported in step D of Example 8 with aldehyde 54 (100 mg, 0.41 mmol) and enamine 66 (100 mg, 0.41 mmol) as reactants. Purification by column chromatography on SiO2 (Petroleum Ether/EtOAc=2:1) afford the title compound 65 as a pale yellow solid. (Yield 65 mg, 39%).

Workup

  1. customThe title compound 65 is prepared
  2. customPurification by column chromatography on SiO2 (Petroleum Ether/EtOAc=2:1)

Sources & evidence

ORD record
ord-174e380100c84c0c83f399a1afdb5d65
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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