Potassium Fluoride → N-(3-(4-bromo-2-nitrophenylamino)-5-(1H-pyrrol-1-yl)phenyl)acetamide

HRID 64110Notes

Reaction equation

HRID 64110 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.[Br:17][C:18]1[CH:23]=[CH:22][C:21](F)=[C:20]([N+:25]([O-:27])=[O:26])[CH:19]=1.[F-].[K+]>CN(C=O)C>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([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:20]([N+:25]([O-:27])=[O:26])[CH:19]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 89500087N-(3-amino-5-pyrrol-1-yl-phenyl)acetamide

Product 1

HCID 89501212N-(3-(4-bromo-2-nitrophenylamino)-5-(1H-pyrrol-1-yl)phenyl)acetamideYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of N-(3-amino-5-pyrrol-1-yl-phenyl)acetamide (5 g, 23.23 mmol) in anhydrous DMF (5 ml), 4-bromo-1-fluoro-2-nitrobenzene (5.11 g, 23.23 mmol) and potassium fluoride (1.35 g, 23.23 mmol) were added. The mixture was stirred at 110° C. for overnight. Then the mixture was brought to RT and DMF was removed under vacuum. Residue was subjected to flash column chromatography (50% ethyl acetate in hexanes) to get the compound in 63% yield (6.1 g).

Workup

  1. customwas brought to RT
  2. customDMF was removed under vacuum
  3. customto get the compound in 63% yield (6.1 g)

Sources & evidence

ORD record
ord-dc74e07674474954a0d5eca265a6d8db
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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