Iodoethane → HCID 16063552, compound

HRID 1993930Notes

Reaction equation

HRID 1993930 reaction equation
[C:1]1([N:7]2[C:15](=[O:16])[C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH2:18][CH3:19]>CN(C=O)C>[CH2:18]([N:8]1[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[C:15](=[O:16])[N:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:19]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 31161752-Phenyl-1,2,4,5,6,7-hexahydro-indazol-3-one

Product 1

HCID 16063552HCID 16063552, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-phenyl-1,2,4,5,6,7-hexahydro-indazol-3-one (0.1 g) in DMF (1 mL) was added iodoethane (0.073 mL) and the mixture was placed into a pressure bomb and sealed. The reaction vessel was then heated in an oil bath to 100° C. over three days. The reaction vessel was then cooled and the DMF was evaporated in vacuo. The residue was dissolved in EtOAc and saturated and washed with saturated sodium bicarbonate solution. The phases were separated and the aqueous solution was extracted with EtOAc another two times at neutral pH. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo to afford a crude residue. Flash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane and 3% AcOH afforded the desired 1-ethyl-2-phenyl-1,2,4,5,6,7-hexahydro-indazol-3-one (0.084 g) as a light brown solid. MS (ESI+): MS (ESI+): 243.4 [M+H]+).

Workup

  1. customsealed
  2. temperatureThe reaction vessel was then cooled
  3. customthe DMF was evaporated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washsaturated and washed with saturated sodium bicarbonate solution
  6. customThe phases were separated
  7. extractionthe aqueous solution was extracted with EtOAc another two times at neutral pH
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customto afford a crude residue
  13. washFlash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane and 3% AcOH

Sources & evidence

ORD record
ord-e943aff45eba4799801c7ac4ca4a0fff
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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