Potassium Fluoride → N-(5-(4-bromo-2-nitrophenylamino)-2',4'-difluorobiphenyl-3-yl)acetamide

HRID 64087Notes

Reaction equation

HRID 64087 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])[CH:7]=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24](F)=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1.[F-].[K+]>CN(C=O)C>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([NH:1][C:2]2[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=3[F:15])[CH:7]=2)=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 89500067N-(5-amino-2',4'-difluorobiphenyl-3-yl)acetamide

Product 1

HCID 89500227N-(5-(4-bromo-2-nitrophenylamino)-2',4'-difluorobiphenyl-3-yl)acetamideYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(5-amino-2′,4′-difluorobiphenyl-3-yl)acetamide (3.0 g, 11.44 mmol), 4-bromo-1-fluoro-2-nitrobenzene (2.52 g, 11.44 mmol, 1.0 eq.) and potassium fluoride (0.663 g, 11.44 mmol, 1.0 eq.) in DMF was heated at 130° C. for 5 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off under reduced pressure and the crude residue was purified by column chromatography (60-120 silica gel, 40% ethyl acetate in hexane) to afford the product in 45% yield (2.4 g).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe crude residue was purified by column chromatography (60-120 silica gel, 40% ethyl acetate in hexane)
  5. customto afford the product in 45% yield (2.4 g)

Sources & evidence

ORD record
ord-433560b0f76a4007946e34609e440cfa
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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