Dimethylformamide → N-[6-(3-fluoro-5-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 1874434Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of N-(6-hydroxy[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (200 mg, 0.917 mmol), 1,3-difluoro-5-nitrobenzene (437 mg, 2.75 mmol), potassium carbonate (380 mg, 2.75 mmol) and N,N-dimethylformamide (6 mL) was stirred at 140° C. for 6 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 collected by filtration and washed with ethyl acetate-hexane to give the title compound (1.59 g, 89%) as a yellow 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
filtrationthe residue was collected by filtration
washwashed with ethyl acetate-hexane

Sources & evidence

ORD record: ord-ca9f14b81e044a2d893d0717f4395e6d
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Reaction notes

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