Potassium Fluoride → N-(5-((5-bromo-3-nitropyridin-2-yl)amino)-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamide

HRID 64150

Reaction equation

HRID 64150 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[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])[CH:7]=1.[Br:20][C:21]1[CH:22]=[C:23]([N+:28]([O-:30])=[O:29])[C:24](Cl)=[N:25][CH:26]=1.[F-].[K+]>CN(C=O)C>[Br:20][C:21]1[CH:22]=[C:23]([N+:28]([O-:30])=[O:29])[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[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=3[F:15])[CH:7]=2)=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 70194125-Bromo-2-chloro-3-nitropyridineHCID 89500157N-(5-amino-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamide

Product 1

HCID 117777719N-(5-((5-bromo-3-nitropyridin-2-yl)amino)-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamideYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(5-amino-2′,6′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (1.4 g, 6.1 mmol), 5-bromo-2-chloro-3-nitropyridine (1.6 g, 6.1 mmol, 1.0 eq.) and potassium fluoride (0.53 g, 9.0 mmol, 1.5 eq.) in DMF (8 ml) was heated at 110° C. for 4 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude product which was purified by column chromatography (60-120 silica gel, 30% Ethyl acetate in hexane) to give the title product in 28% yield (0.8 g).

Workup

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

Sources & evidence

ORD record
ord-617f241a9e4c4fe1aee17f66a38e319f
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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