Potassium Carbonate → 5-[3-(Benzyloxy)-2-fluoro-4-nitrophenoxy]-2-(methylsulfonyl)pyridine

HRID 1188954Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([F:15])=[C:13](F)[CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21]([C:24]1[N:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:14]([F:15])=[C:13]([CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[O:30][C:27]1[CH:26]=[CH:25][C:24]([S:21]([CH3:20])(=[O:23])=[O:22])=[N:29][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(benzyloxy)-3,4-difluoro-1-nitrobenzene (7.65 g), 6-(methylsulfonyl)pyridin-3-ol (5.0 g) and potassium carbonate (4.4 g) in N,N-dimethylformamide (40 mL) was stirred at 90° C. for 5 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with successively water and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=25:75 to 40:60, volume ratio) to give light yellow crystals, which were washed with ethyl acetate-hexane to give the title compound (8.4 g, 69%) as pale yellow crystals.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with successively water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=25:75 to 40:60, volume ratio)
customto give light yellow crystals, which
washwere washed with ethyl acetate-hexane

Sources & evidence

ORD record: ord-168cd5ef4299453f933c46a20bd7ccc2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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