Potassium Carbonate → 2,3-Difluoro-1-(6-methanesulfonyl-pyridin-3-yloxy)-4-nitro-benzene

HRID 13332

Reaction equation

[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O.[F:25][C:26]1[C:31]([F:32])=[C:30](F)[CH:29]=[CH:28][C:27]=1[N+:34]([O-:36])=[O:35]>C(OCC)(=O)C>[F:32][C:31]1[C:26]([F:25])=[C:27]([N+:34]([O-:36])=[O:35])[CH:28]=[CH:29][C:30]=1[O:11][C:8]1[CH:9]=[N:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

112 mg of 6-methanesulfonyl-pyridin-3-ol and 100 mg of potassium carbonate were added to an N-methylpyrrolidinone (3 ml) solution of 135 mg of 2,3,4-trifluoro-nitrobenzene, and the reaction liquid was stirred at 50° C. for 1 hour. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1) to obtain the entitled compound.

Workup

customthe reaction liquid
customThe reaction liquid
washwashed with water and saturated saline in order
dry with materialdried with anhydrous sodium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1)
customto obtain the entitled compound

Sources & evidence

ORD record: ord-f1e825910c5e4810ac501736dcd3ce56
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Linked notes

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