Iodine → HCID 178419333, compound

HRID 2068271Notes

Reaction equation

HRID 2068271 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.[OH-].[K+].[I:13]I.[OH-].[NH4+]>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[I:13]

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 7619295-bromo-1H-indazole

Product 1

HCID 178419333HCID 178419333, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Into a round-bottom flask was dissolved 5-bromo-1H-indazole (1.99 g, 0.0101 mol) in N,N-dimethylformamide (10.0 mL). To this stirred solution was added potassium hydroxide (2.03 g, 0.0362 mol) then a cold solution of iodine (2.82 g, 0.0111 mol) in N,N-dimethylformamide (12.0 mL, 0.155 mol) was added dropwise. The mixture was stirred at room temperature for 2 hours before being added dropwise to an ammonium hydroxide (150 mL, 3.8 mol) solution in water (2.0 L) to give a precipate. The precipitate was collected and dried under vacuum for 18 hours to yield 3.00 g (92%) of 5-bromo-3-iodo-1H-indazole.

Workup

  1. customto give a precipate
  2. customThe precipitate was collected
  3. customdried under vacuum for 18 hours

Sources & evidence

ORD record
ord-9cb786ac72f44da0b2d6d290510af0a9
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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