Iodine → HCID 71280541, compound

HRID 246332Notes

Reaction equation

HRID 246332 reaction equation
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=[N:2]1.[OH-].[K+].[I:13]I>CN(C=O)C>[I:13][C:3]1[C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[NH:1][N:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 12200544HCID 12200544, compound

Product 1

HCID 71280541HCID 71280541, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,4,5,6,7,8-hexahydrocycloheptapyrazole (500 mg, 3.67 mmol) in DMF (8 ml) at room temperature was added powdered potassium hydroxide (618 mg, 11.0 mmol) and iodine (1.86 g, 7.34 mmol). The maroon reaction mixture was stirred at room temperature for 1 h then quenched with aqueous 10% Na2S2O3, diluted with water, and extracted with EtOAc (2×). The combined organics were washed with water (3×), dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography with 20% to 50% EtOAc/hexanes to afford 600 mg (62%) of 3-iodo-1,4,5,6,7,8-hexahydrocycloheptapyrazole as a white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 2.75-2.84 (m, 2H), 2.46-2.55 (m, 2H), 1.80-1.91 (m, 2H), 1.63-1.77 (m, 4H).

Workup

  1. customThe maroon reaction mixture
  2. customthen quenched with aqueous 10% 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
  8. customThe residue was purified by SiO2 chromatography with 20% to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-51874802cdc049d8bcaf0fb5dda7fdd4
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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