Iodine → HCID 178505447, compound

HRID 246072Notes

Reaction equation

HRID 246072 reaction equation
[F: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>[F: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 178423506-Fluoro-1H-indazole

Product 1

HCID 178505447HCID 178505447, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-fluoro-1H-indazole (5.50 g, 40.4 mmol) in DMF (150 ml) at room temperature was added potassium hydroxide (6.8 g, 121 mmol) and iodine (15.4 g, 60.6 mmol). The maroon reaction mixture was stirred at room temperature for 8 h then quenched with 10% aqueous Na2S2O3 and diluted with water. The mixture was extracted with EtOAc (2×). The combined organics were washed with water, sat LiCl, and sat NaCl, then dried over MgSO4 and concentrated to afford 8.6 g (81%) of 6-fluoro-3-iodo-1H-indazole as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.48 (dd, J=8.9, 5.1 Hz, 1H), 7.20 (dd, J=8.9, 2.1 Hz, 1H), 7.02 (td, J=9.1, 2.1 Hz, 1H)

Workup

  1. customThe maroon reaction mixture
  2. customthen quenched with 10% aqueous Na2S2O3
  3. additiondiluted with water
  4. extractionThe mixture was extracted with EtOAc (2×)
  5. washThe combined organics were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-64b729389bda463299c201a3d037ba5a
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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