Potassium Fluoride → HCID 89500093, compound

HRID 64114Notes

Reaction equation

HRID 64114 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:13][C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[CH:9]2)[CH:7]=1.F[C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26].[F-].[K+]>CN(C=O)C>[I:24][C:21]1[CH:22]=[CH:23][C:18]([NH:1][C:2]2[CH:3]=[C:4]([NH:13][C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([N:8]3[CH:9]=[CH:10][CH:11]=[CH:12]3)[CH:7]=2)=[C:19]([N+:25]([O-:27])=[O:26])[CH:20]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 145905821-Fluoro-4-iodo-2-nitrobenzeneHCID 89500087N-(3-amino-5-pyrrol-1-yl-phenyl)acetamide

Product 1

HCID 89500093HCID 89500093, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-amino-5-pyrrol-1-yl-phenyl)acetamide of Example 87(d) (5.0 g, 18.72 mmol), 1-fluoro-4-iodo-2-nitrobenzene (4.02 g, 18.72 mmol, 1.0 eq.) and potassium fluoride (1.08 g, 18.72 mmol, 1.0 eq.) in DMF (30 ml) was heated at 130° C. for 5 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off and the residue was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane) to give the product in 49% yield (4.3 g).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane)
  5. customto give the product in 49% yield (4.3 g)

Sources & evidence

ORD record
ord-c7e163284c504d979c36869d34b50d92
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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