Potassium Fluoride → N-(3-((4-bromo-2-nitrophenyl)amino)-5-(3-fluoropyridin-2-yl)phenyl)acetamide

HRID 64176Notes

Reaction equation

HRID 64176 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([NH:26][C:27](=[O:29])[CH3:28])[CH:16]=[C:17]([C:19]2[C:24]([F:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:18]=1.[F-].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:12][C:13]2[CH:14]=[C:15]([NH:26][C:27](=[O:29])[CH3:28])[CH:16]=[C:17]([C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:18]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 89500089N-(3-amino-5-(3-fluoropyridin-2-yl)phenyl)acetamide

Product 1

HCID 89500273N-(3-((4-bromo-2-nitrophenyl)amino)-5-(3-fluoropyridin-2-yl)phenyl)acetamideYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solution of 4-bromo-1-fluoro-2-nitrobenzene (3.0 g, 13.63 mmol), N-(3-amino-5-(3-fluoropyridin-2-yl)phenyl)acetamide (4.0 g, 16.36 mmol), and potassium fluoride (0.95 g, 16.36 mmol) in DMF was heated at 130° C. for 16 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to yield the title product in 50% yield (3.4 g). 1H NMR (300 MHz, DMSO-d6): δ 8.55 (brs, 1H), 8.23 (brs, 1H), 7.96 (m, 2H), 7.85 (m, 2H), 7.67 (d, 1H), 7.51 (m, 2H), 7.21 (d, 1H), 2.07 (s, 3H).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto afford the crude residue which
  5. customwas purified by column chromatography (60-120 silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2f04c452ef174e25bf970745daefbe87
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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