Pyrazole → N-(3-nitro-5-(1H-pyrazol-1-yl)phenyl)acetamide

HRID 64120

Reaction equation

HRID 64120 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[NH:15]1[CH:19]=[CH:18][CH:17]=[N:16]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu-]=O>[N+:8]([C:6]1[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([N:15]2[CH:19]=[CH:18][CH:17]=[N:16]2)[CH:7]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Product 1

HCID 117777661N-(3-nitro-5-(1H-pyrazol-1-yl)phenyl)acetamideYield 86%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (10 g, 38.6 mmol) in DMF (100 ml) were added pyrazole (5.26 g, 77.2 mmol, 2.0 eq.), copper(I) oxide (1.104 g, 7.72 mmol, 0.2 eq.) and cesium carbonate (25.15 g, 77.2 mmol, 2.0 eq.) and the mixture was heated at 120° C. for 16 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 over silica gel (30% ethyl acetate in hexane) to afford the compound in 86% yield (8.2 g). 1H NMR (300 MHz, DMSO-d6): δ 10.62 (s, 1H), 8.7 (d, 1H), 8.5-8.48 (m, 2H), 8.32 (t, 1H), 7.84 (d, 1H), 6.62 (t, 1H), 2.08 (s, 3H); LC-MS (ESI): Calculated mass: 246.22; Observed mass: 247.1 [M+H]+ (rt: 0.6 min).

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 over silica gel (30% ethyl acetate in hexane)
  5. customto afford the compound in 86% yield (8.2 g)
  6. custom247.1 [M+H]+ (rt: 0.6 min)

Sources & evidence

ORD record
ord-9ed3e0602a6e4738aa987771f44db444
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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