Iodine → 3-Iodo-4,5,6,7-tetrahydro-1H-indazole

HRID 868882Notes

Reaction equation

HRID 868882 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[N:2]1.[OH-].[K+].[I:12]I>CN(C=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>[I:12][C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[NH:1][N:2]=1

Participants

6

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 753174,5,6,7-tetrahydro-1H-indazole

Product 1

HCID 712807353-Iodo-4,5,6,7-tetrahydro-1H-indazoleYield 84.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a suspension of 4,5,6,7-tetrahydroindazole (700 mg, 5.7 mmol) and KOH (1.2 g, 21.5 mmol) in DMF (20 mL) was added I2 (2.9 g, 11.5 mmol) at 0° C., and the reaction was stirred overnight while warming to rt. The reaction mixture was diluted with sat. Na2S2O3, extracted with EtOAc (50 mL×3), washed with brine (50 mL), dried (MgSO4), and concentrated to give 1.2 g (83%) of the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.73-1.84 (4H, m), 2.40 (2H, t, J=5.6 Hz), 2.54 (2H, t, J=6.0 Hz).

Workup

  1. extractionextracted with EtOAc (50 mL×3)
  2. washwashed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ac4f77f0466b4efcb8a6d4cf496f700e
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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