2-[(Methylsulfonyl)methyl]-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridine → 4-({6-[(Methylsulfonyl)methyl]pyridin-3-yl}oxy)-2-(tetrahydro-2H-pyran-4-yloxy)aniline

HRID 1042117Notes

Reaction equation

HRID 1042117 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([O:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:14]=2)=[CH:8][N:7]=1)(=[O:4])=[O:3]>C(O)C.[C].[Pd]>[CH3:1][S:2]([CH2:5][C:6]1[N:7]=[CH:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([O:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:14]=2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 667262242-[(Methylsulfonyl)methyl]-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridine

Product 1

HCID 667261624-({6-[(Methylsulfonyl)methyl]pyridin-3-yl}oxy)-2-(tetrahydro-2H-pyran-4-yloxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[(methylsulfonyl)methyl]-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridine (22 g) in ethanol (250 mL) was added 10% palladium carbon (2 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 15 hr. Palladium carbon was removed, and the residue was concentrated under reduced pressure to give the title compound (20 g, yield 100%) as a colorless amorphous solid.

Workup

  1. customPalladium carbon was removed
  2. concentrationthe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-84b8d44a75bb4f03baf5020423443b20
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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