2-Chloro-5-nitropyridine → 2,2,2-trifluoro-N-{2-fluoro-5-[methyl(5-nitropyridin-2-yl)amino]phenyl}acetamide

HRID 2366749Notes

Reaction equation

HRID 2366749 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]([F:26])([F:25])[C:13]([NH:15][C:16]1[CH:21]=[C:20]([NH:22][CH3:23])[CH:19]=[CH:18][C:17]=1[F:24])=[O:14]>CN(C)C=O.C(OCC)(=O)C>[F:26][C:12]([F:11])([F:25])[C:13]([NH:15][C:16]1[CH:21]=[C:20]([N:22]([CH3:23])[C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH:19]=[CH:18][C:17]=1[F:24])=[O:14]

Participants

5

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 866460552,2,2-trifluoro-N-[2-fluoro-5-(methylamino)phenyl]acetamide

Product 1

HCID 866460542,2,2-trifluoro-N-{2-fluoro-5-[methyl(5-nitropyridin-2-yl)amino]phenyl}acetamideYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-5-nitropyridine (201 mg, 1.27 mmol) and 2,2,2-trifluoro-N-[2-fluoro-5-(methylamino)phenyl]acetamide (300 mg, 1.27 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at 140° C. for 22 hr. The reaction mixture was cooled to room temperature, suspended in ethyl acetate (5 mL), washed with saturated aqueous sodium hydrogen carbonate solution (5 mL) and saturated brine (5 ml), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate/hexane to give the title compound (221 mg, 49%) as yellow crystals.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution (5 mL) and saturated brine (5 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8caa9093a80449aa8ade28f2f4762bb9
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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