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

HRID 245974Notes

Reaction equation

HRID 245974 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:10][C:9]2[NH:8][N:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[OH-].[K+].[I:14]I>CN(C=O)C>[I:14][C:6]1[C:5]2[CH2:4][CH2:3][C:2]([CH3:11])([CH3:1])[CH2:10][C:9]=2[NH:8][N:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 585504376,6-Dimethyl-4,5,6,7-tetrahydro-1H-indazole

Product 1

HCID 585504063-Iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazoleYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole (0.50 g, 3.33 mmol) in DMF (8 mL) at room temperature was added powdered potassium hydroxide (560 mg, 10.0 mmol) and iodine (1.69 g, 6.66 mmol). The maroon reaction mixture was stirred at room temperature for 45 min then quenched with 10% aqueous Na2S2O3, diluted with water and extracted with EtOAc (2×). The combined organics were washed with water (3×), dried over MgSO4 and concentrated to afford 920 mg (99%) of 3-iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole as a light yellow waxy solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 2.44 (s, 2H), 2.35 (t, J=6.4 Hz, 2H), 1.55 (t, J=6.4 Hz, 2H), 1.01 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-3c9e1ded6f0d44758b418cee7e79e8b9
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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