6-Nitroindazole → HCID 90308747, compound

HRID 2283676Notes

Reaction equation

HRID 2283676 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl[C:16]([F:21])([F:20])C([O-])=O.[Na+]>CN1CCCC1=O.C(OCC)(=O)C>[F:20][CH:16]([F:21])[N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=2)[CH:10]=[N:11]1.[F:20][CH:16]([F:21])[N:11]1[CH:10]=[C:9]2[C:13]([CH:14]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[CH:8]2)=[N:12]1

Participants

7

Reactant 3

HCID 242396-NitroindazoleHCID 24758Sodium hydrideHCID 2734985Sodium chlorodifluoroacetate

Product 2

HCID 90308747HCID 90308747, compoundHCID 90309015HCID 90309015, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

60% Sodium hydride (including 40% liquid paraffin as an additive) (1.2 g) was added to a solution of 6-nitro-1H-indazole (5.90 g) and sodium chlorodifluoroacetate (9.15 g) in N-methylpyrrolidinone (100 ml). Thereafter, the reaction solution was stirred at room temperature for 15 minutes, and further stirred at 100° C. for 30 minutes. The reaction solution was diluted with ethyl acetate, and washed successively with water and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain 1-(difluoromethyl)-6-nitro-1H-indazole and 2-(difluoromethyl)-6-nitro-2H-indazole as a mixture.

Workup

  1. stirringfurther stirred at 100° C. for 30 minutes
  2. washwashed successively with water
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. customThe residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

Sources & evidence

ORD record
ord-be8624023ef944da9dcabc7eb152c1d9
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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