Iodine → HCID 178477877, compound

HRID 246642Notes

Reaction equation

HRID 246642 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[OH-].[K+].[I:13]I>CN(C=O)C>[Cl: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 14797Potassium HydroxideHCID 4175246-chloro-1H-indazole

Product 1

HCID 178477877HCID 178477877, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 6-chloro-1H-indazole (2 g, 13.1 mmol), KOH (2.2 g, 39.3 mmol) and I2 (6.6 g, 26.2 mmol) in dry DMF (20 mL) was heated to 30° C. for 16 hours. Reaction quenched with water, product was extracted with ethyl acetate (150 mL), organic phase washed with water (3×10 mL), brine (2×10 mL) and dried over Na2SO4, then filtered and concentrated to afford 6-chloro-3-iodo-1H-indazole (3.0 g, 83%) as a yellow solid. LCMS: (M+H)+=279.

Workup

  1. customReaction
  2. customquenched with water, product
  3. extractionwas extracted with ethyl acetate (150 mL), organic phase
  4. washwashed with water (3×10 mL), brine (2×10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ba94e7cba97045b59f9c65c67025b88a
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…