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

HRID 1042123Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([O:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[CH:13]=2)=[CH:7][N:6]=1)(=[O:4])=[O:3]>C(O)C.O1CCCC1.[C].[Pd]>[CH3:1][S:2]([C:5]1[N:6]=[CH:7][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[CH:13]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-(methylsulfonyl)-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridine (25.8 g) in ethanol (250 mL) and tetrahydrofuran (250 mL) was added 10% palladium carbon (3 g), and the mixture was stirred under hydrogen pressure of 0.5 MPa at 50° C. for 6 hr. Palladium carbon was removed, and the mixture was concentrated under reduced pressure to give the title compound (24 g, yield 100%) as a white powder.

Workup

customPalladium carbon was removed
concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-ea2c9a2a089c4807ad21ec2566f554a1
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557805B2

Reaction notes

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