Iodine → HCID 178458234, compound

HRID 246317Notes

Reaction equation

HRID 246317 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:13])([CH3:12])[CH3:11])[CH:3]=[N:2]1.[I:14]I.[OH-].[K+]>CN(C=O)C>[I:14][C:3]1[C:4]2[C:9](=[C:8]([C:10]([OH:13])([CH3:11])[CH3:12])[CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 84655566HCID 84655566, compound

Product 1

HCID 178458234HCID 178458234, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask, 2-(1H-indazol-7-yl)-propan-2-ol (204 mg, 1.16 mmol) was dissolved in DMF (3 ml) and iodine (588 mg, 2.32 mmol) and potassium hydroxide (251 mg, 4.48 mmol) were added. The dark brown suspension was stirred at room temperature for 5 h then quenched with 10% aqueous NaHSO3 and extracted with a mixture of diethyl ether and EtOAc (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated to afford 2-(3-iodo-1H-indazol-7-yl)-propan-2-ol as a light yellow oil which was used without further purification.

Workup

  1. customthen quenched with 10% aqueous NaHSO3
  2. extractionextracted with a mixture of diethyl ether and EtOAc (2×)
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8e83257780664d03832ad0e42319bd06
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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