Water → HCID 58267997, compound

HRID 2283669Notes

Reaction equation

HRID 2283669 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1.[CH3:16]I.O>CN(C=O)C>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH3:16])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1.[Br:3][C:4]1[CH:5]=[C:6]([N+:13]([O-:15])=[O:14])[C:7]2[C:11]([CH:12]=1)=[N:10][N:9]([CH3:16])[CH:8]=2

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 247280596-bromo-4-nitro-1H-indazole

Product 2

HCID 58267997HCID 58267997, compoundHCID 903087036-bromo-2-methyl-4-nitro-2H-indazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

60% Sodium hydride (including 40% liquid paraffin as an additive) (213 mg) was added to a solution of 6-bromo-4-nitro-1H-indazole (901 mg) in DMF (19 ml) in an ice bath. Subsequently, the reaction solution was stirred at 0° C. for 15 minutes, then methyl iodide (0.35 ml) was added, and the reaction solution was allowed to react at room temperature for 11 hours. The reaction solution was poured into water, and the deposited precipitate was filtrated to obtain a crude product. The crude product was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 6-bromo-1-methyl-4-nitro-1H-indazole and 6-bromo-2-methyl-4-nitro-2H-indazole as a yellow solid, respectively.

Workup

  1. customto react at room temperature for 11 hours
  2. filtrationthe deposited precipitate was filtrated
  3. customto obtain a crude product
  4. customThe crude product was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cbd09c06eb044f8cad96773192b6ea41
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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