Iodine → HCID 178419314, compound

HRID 2066418Notes

Reaction equation

HRID 2066418 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[OH-].[Na+].[I:13]I>O1CCOCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 178424716-Bromo-1H-indazole

Product 1

HCID 178419314HCID 178419314, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-bromo-1H-indazole (10 g, 50.8 mmol, commercially available) in dioxane (200 ml) was treated with 3N aqueous NaOH (100 ml). The vigorously stirred mixture was treated with iodine (27.1 g, 107 mmol), added portionwise over 5 minutes then stirred for 60 minutes. The reaction was quenched with 200 ml of 20% citric acid solution, followed by 160 ml of saturated NaHSO3 solution, then partitioned between ethyl acetate and water. The organic extract was dried with MgSO4 and concentrated to a solid which was triturated with ether and pentane to afford the title compound.

Workup

  1. additionadded portionwise over 5 minutes
  2. customThe reaction was quenched with 200 ml of 20% citric acid solution
  3. custompartitioned between ethyl acetate and water
  4. extractionThe organic extract
  5. dry with materialwas dried with MgSO4
  6. concentrationconcentrated to a solid which
  7. customwas triturated with ether and pentane

Sources & evidence

ORD record
ord-aef1a90be21845caa49e34702b288313
Source dataset
uspto-grants-2012_10
Patent number
US08293738B2

Reaction notes

Loading…