HCID 58237077, compound → HCID 67118481, compound

HRID 1188903Notes

Reaction equation

HRID 1188903 reaction equation
C([O:8][C:9]1[CH:15]=[C:14]([O:16][C:17]2[CH:18]=[N:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=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:18]=[N:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[CH:15][C:9]=1[OH:8]

Participants

5

Reactant 1

HCID 58237077HCID 58237077, compound

Product 1

HCID 67118481HCID 67118481, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(benzyloxy)-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}aniline (26 g) in a mixture of tetrahydrofuran (200 mL) and methanol (50 mL) was added palladium on carbon (5 g, 10 wt %, wet), and the mixture was stirred at room temperature for 5 h under hydrogen atmosphere. The mixture was filtered to remove the catalyst and the filtrate was concentrated under reduced pressure. The residual oil was solidified with diethyl ether, and the solid was washed with ethyl acetate-diethyl ether to give the title compound (17.28 g, 88%) as a grayish solid. MS 281 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washthe solid was washed with ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-70e2241c4b4e43958006051340462396
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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