Potassium Hydroxide → 1-(2,4-difluorobenzyl)-4-nitro-1H-indazole

HRID 706702Notes

Reaction equation

HRID 706702 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].[OH-].[K+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24]>CC(C)=O>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[CH2:16][N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[N:7]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 180574-NitroindazoleHCID 902971-(Bromomethyl)-2,4-difluorobenzene

Product 1

HCID 679763271-(2,4-difluorobenzyl)-4-nitro-1H-indazoleYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-nitro-1H-indazole (0.200 g, 1.226 mmol) in acetone (3 mL) cooled to 0° C., was added KOH (0.103 g, 1.839 mmol). After 15 minutes at 0° C., 1-(bromomethyl)-2,4-difluorobenzene (0.173 mL, 1.349 mmol) was added. The mixture was allowed to stir at ambient temperature overnight, concentrated and the residue purified on silica gel (5-25% EtOAc in hexanes) to provide 1-(2,4-difluorobenzyl)-4-nitro-1H-indazole (0.142 g, 40% yield) as a pale yellow solid.

Workup

  1. concentrationconcentrated
  2. customthe residue purified on silica gel (5-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-81fda1e17ce546f09635e75cdf6adb4c
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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