Iodine → HCID 178419333, compound

HRID 1465690Notes

Reaction equation

HRID 1465690 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.[I:11]I.[OH-].[K+].OS([O-])=O.[Na+]>CN(C=O)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[I:11]

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 7619295-bromo-1H-indazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 178419333HCID 178419333, compoundYield 131.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-1H-indazole (8.00 g, 40.6 mmol) in DMF (200 ml), was added I2 (20.61 g, 81.2 mmol) and KOH (8.54 g, 152.3 mmol) successively. The reaction was stirred at room temperature for 3 h. The mixture was then poured into aqueous NaHSO3 and extracted with Et2O (3×150 ml). The combined organic layers were washed with water (3×150 ml) and brine (3×150 ml). It was dried over anhydrous Na2SO4 and evaporated to dryness to give crude product 5-bromo-3-iodo-1H-indazole (17.21 g).

Workup

  1. extractionextracted with Et2O (3×150 ml)
  2. washThe combined organic layers were washed with water (3×150 ml) and brine (3×150 ml)
  3. dry with materialIt was dried over anhydrous Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-335a5ecb2c00424cb8cd03ff2cc3b02e
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

Loading…