Potassium Fluoride → Methyl 4-((5-acetamido-2',4'-difluoro-[1,1'-biphenyl]-3-yl)amino)-3-nitrobenzoate

HRID 64185Notes

Reaction equation

HRID 64185 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.F[C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[N+:31]([O-:33])=[O:32].[F-].[K+]>CN(C=O)C>[C:17]([NH:16][C:4]1[CH:3]=[C:2]([NH:1][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[N+:31]([O-:33])=[O:32])[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])[CH:5]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 89500067N-(5-amino-2',4'-difluorobiphenyl-3-yl)acetamide

Product 1

HCID 117777463Methyl 4-((5-acetamido-2',4'-difluoro-[1,1'-biphenyl]-3-yl)amino)-3-nitrobenzoateYield 48.78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(5-amino-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (1.0 g, 3.813 mmol), methyl 4-fluoro-3-nitrobenzoate (0.835 g, 4.194 mmol, 1.1 eq.) and potassium fluoride (0.265 g, 4.457 mmol, 1.2 eq.) 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 give the crude residue which was purified by column chromatography (60-120 silica gel, 40% ethyl acetate in hexane) to give the product in 48.78% yield (0.82 g).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-e0cfa6581e6347aa88ab0aec61b5ea45
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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