Iodine → HCID 178477877, compound

HRID 245791Notes

Reaction equation

HRID 245791 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.[I:11]I.[OH-].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:11])=[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 102.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask, 6-chloro-1H-indazole (90 mg, 0.59 mmol) was dissolved in DMF (1.4 mL). Iodine (300 mg, 1.18 mmol) was added followed by potassium hydroxide (128 mg, 2.28 mmol). The dark reaction mixture was stirred at room temperature for 3 h then was quenched with 10% aq NaHSO3 and extracted with diethyl ether (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to give 169 mg (98%) of 6-chloro-3-iodo-1H-indazole as an orange solid.

Workup

  1. customThe dark reaction mixture
  2. customthen was quenched with 10% aq NaHSO3
  3. extractionextracted with diethyl ether (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-899ed2f2365442eeb3ab577738bd5a40
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…