5-Nitroindazole → HCID 178526490, compound

HRID 1823914Notes

Reaction equation

HRID 1823914 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].[Br:13]Br>C(O)(=O)C>[Br:13][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1

Participants

4

Reactant 2

HCID 215015-NitroindazoleHCID 24408Bromine

Product 1

HCID 178526490HCID 178526490, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

5-Nitroindazole (10 g, 61.3 mmol) was dissolved in acetic acid (170 mL) and the mixture heated to 80° C. Bromine (3.1 mL, 60.7 mmol) was added slowly and the mixture heated to reflux. After 2 hours, the reaction mixture was allowed to cool to room temperature, and the resulting precipitate filtered off. Additional product was isolated by concentrating the filtrate, partitioning the residue between chloroform and saturated sodium bicarbonate solution, separating and drying the organic phase over sodium sulfate. Concentration gave a solid which was combined with the original precipitate to give the title compound as a yellow solid (11.4 g, 77%). 1H NMR δ 7.74 (1H, d), 8.21 (1H, dd), 8.40 (1H, d), 14.06 (1H, brs); MS (ES−) m/e=240.

Workup

  1. temperaturethe mixture heated to reflux
  2. temperatureto cool to room temperature
  3. filtrationthe resulting precipitate filtered off
  4. customAdditional product was isolated
  5. concentrationby concentrating the filtrate
  6. custompartitioning the residue between chloroform and saturated sodium bicarbonate solution
  7. customseparating
  8. dry with materialdrying the organic phase over sodium sulfate
  9. concentrationConcentration
  10. customgave a solid which

Sources & evidence

ORD record
ord-11e6ac8c8ddd4a7d9d418a9a9a11ce87
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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