Potassium Fluoride → N-(3-bromo-5-((4-(1-methyl-1H-pyrazol-4-yl)-2-nitrophenyl)amino)phenyl) acetamide

HRID 64165Notes

Reaction equation

HRID 64165 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[NH2:17][C:18]1[CH:19]=[C:20]([NH:25][C:26](=[O:28])[CH3:27])[CH:21]=[C:22]([Br:24])[CH:23]=1.[F-].[K+]>CN(C=O)C>[Br:24][C:22]1[CH:21]=[C:20]([NH:25][C:26](=[O:28])[CH3:27])[CH:19]=[C:18]([NH:17][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=3)=[CH:4][C:3]=2[N+:14]([O-:16])=[O:15])[CH:23]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 67240182HCID 67240182, compoundHCID 895012214-(4-fluoro-3-nitrophenyl)-1-methyl-1H-pyrazole

Product 1

HCID 89501148N-(3-bromo-5-((4-(1-methyl-1H-pyrazol-4-yl)-2-nitrophenyl)amino)phenyl) acetamideYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-fluoro-3-nitrophenyl)-1-methyl-1H-pyrazole (1.6 g, 7.239 mmol), N-(3-amino-5-bromophenyl)acetamide (1.98 g, 8.687 mmol) and potassium fluoride (0.503 g, 8.687 mmol) in DMF was heated at 130° C. for 48 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane) to yield the title product in 35% yield (1.1 g); LC-MS (API): Calculated mass: 430.1; Observed mass: 432 [M+H]+ (rt: 1.50 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto afford the crude residue which
  5. customwas purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-eef84d3976bb486fbd6842c15f625758
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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