(2E)-2-[(3-bromo-4-pyridyl)-methylene]-6-methoxy-tetralin-1-one → 2-[(3-Bromo-4-pyridyl)methyl]-6-methoxy-tetralin-1-one
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1/[CH:8]=[C:9]1/[C:10](=[O:21])[C:11]2[C:16]([CH2:17][CH2:18]/1)=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2>CCO.[Pt]>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]1=[O:21]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Pt/C (5 wt % loading, 200 mg) was added to a stirred solution of the compound 87 (2.0 g, 5.81 mmol) in EtOH (58 mL) at room temperature. The resulting suspension was stirred for 4 hours under H2 atmosphere (1 atm) then filtered over Celite, rinsed with dichloromethane and concentrated to dryness. The crude residue was purified by column chromatography on SiO2 (gradient of EtOAc in petroleum ether) to afford the title compound 99 (Yield 2.0 g, 99%).