Iodine → HCID 178519424, compound

HRID 246311Notes

Reaction equation

HRID 246311 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][OH:11])[CH:3]=[N:2]1.[OH-].[K+].[I:14]I>CN(C=O)C>[I:14][C:3]1[C:4]2[C:9](=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 44119262(1H-Indazol-7-yl)methanol

Product 1

HCID 178519424HCID 178519424, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask, (1H-indazol-7-yl)-methanol (572 mg, 3.09 mmol) was dissolved in DMF (8 ml) and potassium hydroxide (671 mg, 12.0 mmol) and iodine (1.57 g, 6.18 mmol) were added. The dark brown suspension was stirred at room temperature overnight then quenched with aqueous 10% Na2S2O3 and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated to give 433 mg (51%) of (3-iodo-1H-indazol-7-yl)-methanol as a light yellow solid.

Workup

  1. customthen quenched with aqueous 10% Na2S2O3
  2. extractionextracted with diethyl ether (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-30be149e08a342d983a0f9eeefb1b488
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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