Hydrochloric Acid → 2-(Methylsulfonyl)-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridine

HRID 1042122Notes

Reaction equation

F[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([CH:14]=1)[O:7][CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH3:18][S:19]([C:22]1[N:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[CH3:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([O:28][C:2]2[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([O:7][CH:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:14]=2)=[CH:26][N:27]=1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 4-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyran (19.5 g) and 6-(methylsulfonyl)pyridin-3-ol (14 g) in N,N-dimethylformamide (250 mL) was added potassium carbonate (22.3 g), and the mixture was stirred at 110° C. for 4 hr. 1N HCl was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=0:100 to 50:50, volume ratio) to give the title compound (26.4 g, yield 83%) as a yellow solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe obtained crude product

Sources & evidence

ORD record: ord-9912f07894e842b8b1ea9937136b589b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557805B2

Reaction notes

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