Dimethylformamide → 1,3-dimethyl-N-{3-[(5-nitropyridin-2-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

HRID 1874379

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-(3-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (1.58 g, 6.83 mmol), 2-chloro-5-nitropyridine (1.03 g, 6.51 mmol), potassium carbonate (1.42 g, 10.2 mmol) and N,N-dimethylformamide (10 mL) was stirred at 60° C. for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=70/30→0/100) to give the title compound (2.26 g, 94%) as a white solid.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by column chromatography (hexane/ethyl acetate=70/30→0/100)

Sources & evidence

ORD record: ord-418d69c0ffec416197ccf63349b6402e
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Linked notes

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