Potassium Carbonate → HCID 58237034, compound

HRID 1188901Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13](F)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][S:20]([C:23]1[N:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[O:29][C:26]1[CH:25]=[CH:24][C:23]([S:20]([CH3:19])(=[O:22])=[O:21])=[N:28][CH:27]=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)-4-fluoro-1-nitrobenzene (21.0 g), 6-(methylsulfonyl)pyridin-3-ol (14.7 g) and potassium carbonate (12.2 g) in N,N-dimethylformamide (130 mL) was stirred at 90° C. for 5 h and then at 60° C. for 15 h. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and aqueous citric acid. The organic layer was washed successively with water and brine, dried (MgSO4), filtered, and concentrated to give light yellow crystals, which were washed with ethyl acetate-hexane to give the title compound (28.0 g, 82%) as pale yellow crystals. MS 401 (MH+).

Workup

waitat 60° C. for 15 h
concentrationThe reaction mixture was concentrated
customthe residue was partitioned between ethyl acetate and aqueous citric acid
washThe organic layer was washed successively with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give light yellow crystals, which
washwere washed with ethyl acetate-hexane

Sources & evidence

ORD record: ord-fb93354638634b29b754912624fd7125
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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