2-(Benzyloxy)-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}aniline → 2-Amino-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}phenol
Reaction equation
C([O:8][C:9]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][N:18]=2)[CH:13]=[CH:12][C:10]=1[NH2:11])C1C=CC=CC=1>O1CCCC1.CO.[Pd]>[NH2:11][C:10]1[CH:12]=[CH:13][C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][N:18]=2)=[CH:15][C:9]=1[OH:8]Participants
5
Procedure
To a solution of 2-(benzyloxy)-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}aniline (46 g) in a mixture of tetrahydrofuran (400 mL) and methanol (150 mL) was added palladium on carbon (7 g, 10 weight %, wet), and the mixture was stirred at room temperature for 15 h under hydrogen atmosphere. The mixture was filtered to remove the catalyst and the filtrate was concentrated. The residual solid was washed with methanol-diethyl ether to give the title compound (26.91 g, 84%) as a greenish-gray solid. MS 281 (MH+).
Workup
- filtrationThe mixture was filtered
- customto remove the catalyst
- concentrationthe filtrate was concentrated
- washThe residual solid was washed with methanol-diethyl ether
Sources & evidence
- ORD record
- ord-26c96f9b8eec4c2a821f341079c826a4
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673942B2
Reaction notes
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