N-[3-Fluoro-4-({1-[(4-methylphenyl)sulfonyl]-3-vinyl-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide → N-[4-({3-Ethyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:30][C:31](=[O:33])[CH3:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:16]=[C:17]([CH:18]=[CH2:19])[C:10]=12>C(O)C.[Pd]>[CH2:18]([C:17]1[C:10]2[C:11](=[N:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:30][C:31](=[O:33])[CH3:32])=[CH:3][C:2]=2[F:1])[N:15]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)(=[O:21])=[O:22])[CH:16]=1)[CH3:19]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
82 mg (0.18 mmol) of N-[3-fluoro-4-({1-[(4-methylphenyl)sulfonyl]-3-vinyl-1H-pyrrolo[2,3-b]-pyridin-4-yl}oxy)phenyl]acetamide are dissolved in 25 ml of ethanol. 19 mg (0.02 mmol) of 10% palladium-on-carbon are added, and the mixture is hydrogenated under a hydrogen atmosphere of 1.5 atm overnight. The mixture is then filtered through Celite® and the solvent is removed under reduced pressure. The product is reacted further without further purification.
Workup
- customis hydrogenated under a hydrogen atmosphere of 1.5 atm overnight
- filtrationThe mixture is then filtered through Celite®
- customthe solvent is removed under reduced pressure
- customThe product is reacted further without further purification
Sources & evidence
- ORD record
- ord-1c0c8b76cb994e32a2fae4866b4a866b
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329716B2
Reaction notes
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