Bromine → HCID 178478419, compound

HRID 268869Notes

Reaction equation

HRID 268869 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[Br:11]Br>CC(O)=O.CCOC(C)=O>[Br:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][N:3]=[C:2]2[Cl:1]

Participants

5

Reactant 2

HCID 24408BromineHCID 958943-Chloro-1H-indazole

Product 1

HCID 178478419HCID 178478419, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature solution of 3-chloro-1H-indazole (10.0 g, 65.5 mmol) in AcOH (250 ml) was added Br2 (3.54 ml, 68.8 mmol) dropwise. The reaction mixture was stirred at room temperature for 18 hours, then diluted with EtOAc (500 ml), washed with aqueous NaOH solution (10%), saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered, concentrated, and the residue was recrystallized from toluene. The solid was washed with hexanes and dried in vacuo affording 5-Bromo-3-chloro-1H-indazole CCXIV as a white solid (54% yield).

Workup

  1. washwashed with aqueous NaOH solution (10%), saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was recrystallized from toluene
  6. washThe solid was washed with hexanes
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7e4ebfc6579e44509b9a6fc46fe0eaf7
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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