2-((2S)-4-methyl-1-((5-vinyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-yl)isoindoline-1,3-dione → 2-((2S)-1-(5-ethyl-5H-chromeno[3,4-c]pyridin-8-yloxy)-4-methylpentan-2-yl)isoindoline-1,3-dione
Reaction equation
[CH3:1][CH:2]([CH3:34])[CH2:3][C@H:4]([N:23]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]1=[O:33])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:20]3[C:15](=[CH:16][N:17]=[CH:18][CH:19]=3)[CH:14]([CH:21]=[CH2:22])[O:13][C:11]=2[CH:12]=1>CO.[Pd]>[CH2:21]([CH:14]1[C:15]2=[CH:16][N:17]=[CH:18][CH:19]=[C:20]2[C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][C@@H:4]([N:23]3[C:31](=[O:32])[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]3=[O:33])[CH2:3][CH:2]([CH3:34])[CH3:1])=[CH:12][C:11]=2[O:13]1)[CH3:22]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 2-((2S)-4-methyl-1-((5-vinyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-yl)isoindoline-1,3-dione (0.3 g, 0.660 mmol) in methanol (15 mL) was added 10% palladium on carbon (0.070 g, 0.660 mmol). The resultant mixture was stirred at room temperature under a hydrogen atmosphere (1 atm) for 12 h. The reaction mixture was then filtered through celite and concentrated under reduced pressure to yield crude 2-((2S)-1-(5-ethyl-5H-chromeno[3,4-c]pyridin-8-yloxy)-4-methylpentan-2-yl)isoindoline-1,3-dione (0.28 g, 0.221 mmol, 33% crude yield); LCMS (ESI) m/e 457.2 [(M+H)+, calcd for C28H29N2O4 457.2]; LC/MS retention time (Method C): tR=2.32 min.
Workup
- filtrationThe reaction mixture was then filtered through celite and
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9af0f9ca4f9d4cdaad24833a79bfae0f
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969564B2
Reaction notes
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