N-{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide → N-{5-[(5-aminopyridin-2-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide

HRID 1800540Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)=[CH:6][C:5]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])=[C:4]([F:25])[CH:3]=1>C(O)(=O)C>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[C:2]([Cl:1])=[CH:3][C:4]([F:25])=[C:5]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH:6]=2)=[N:10][CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (600 mg, 1.58 mmol), reduced iron (452 mg, 8.09 mmol) and acetic acid (10 mL) was stirred at 60° C. for 1.5 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (20 mL), washed with saturated aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→34/66) to give the title compound (357 mg, 65%) as a white powder.

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate (20 mL)
washwashed with saturated aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (10 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→34/66)

Sources & evidence

ORD record: ord-95518fe692f844e19228643dcfd4bc27
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344135B2

Reaction notes

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