5-bromo-1H-indazole → HCID 178478419, compound

HRID 490103Notes

Reaction equation

HRID 490103 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[Cl:11]NC(=O)CCC(N)=O>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[Cl:11]

Participants

4

Reactant 2

HCID 7619295-bromo-1H-indazoleHCID 15238416N-chlorosuccinamide

Product 1

HCID 178478419HCID 178478419, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromoindazole 162 (0.234 g, 1.19 mmol.) in anhydrous acetonitrile (8 mL) was added N-chlorosuccinamide (0.174 g, 1.31 mmol.). The reaction mixture was heated at 60° C. for 2 hours. The organic solvent was evaporated under reduced pressure. Ethyl acetate (100 mL) was added. The organic layer was washed was 1N sodium hydroxide solution, water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to yield 5-bromo-3-chloroindazole 163 (0.26 g, 1.13 mmol.). The crude product was used in the next step without further purification.

Workup

  1. customThe organic solvent was evaporated under reduced pressure
  2. additionEthyl acetate (100 mL) was added
  3. washThe organic layer was washed
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customThe organic solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9b660676734242879a1dabe23afbbdaa
Source dataset
uspto-grants-2009_05
Patent number
US07528132B2

Reaction notes

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