Hydrochloric Acid → HCID 59397241, compound

HRID 2076357Notes

Reaction equation

HRID 2076357 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:19](=[O:20])[CH:18]([C:21](OCC)=O)[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].BrC[CH2:36][F:37].[OH-].[Na+].Cl>CC(N(C)C)=O.C(OCC)C>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:19](=[O:20])[CH:18]([CH2:21][CH2:36][F:37])[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 14798Sodium Hydroxide2×HCID 59397246Ethyl 2-benzyl-6-oxo-2,6,7,8-tetrahydrocyclopenta[e]indazole-7-carboxylate

Product 1

HCID 59397241HCID 59397241, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 2-benzyl-6-oxo-2,6,7,8-tetrahydrocyclopenta[e]indazole-7-carboxylate (crude product from the previous step, 14 g, approximately 39 mmol) in 160 mL of dimethylacetamide were added potassium carbonate (11 g, 80 mmol), potassium iodide (13.3 g, 80 mmol) and 1-bromo-2-fluoroethane (3.8 mL, 51 mmol) and the stirred mixture was heated at 65° C. under nitrogen for 19 hours. The heating bath was removed and the reaction mixture was allowed to cool for 40 minutes and then water (160 mL) and TIM (160 mL) were added followed by 5N aqueous sodium hydroxide (24 mL, 120 mmol). After 3 hours, additional 5N aqueous sodium hydroxide (5 mL, 25 mmol) was added. After 30 minutes more, analysis of an aliquot by LC/MS showed the reaction to be complete and 1N aqueous HCl (150 mL) was added. The reaction mixture was extracted thoroughly with ethyl acetate and the combined extracts were washed with 5% aqueous NaHCO3 and brine and dried over MgSO4. Evaporation of the solvent under vacuum gave an oil which was twice treated with ethyl ether and evaporated under vacuum to give 2-benzyl-7-(2-fluoroethyl)-7,8-dihydrocyclopenta[e]indazol-6(2H)-one as a brown solid.

Workup

  1. customThe heating bath was removed
  2. temperatureto cool for 40 minutes
  3. additionwater (160 mL) and TIM (160 mL) were added
  4. waitAfter 30 minutes more
  5. customthe reaction
  6. extractionThe reaction mixture was extracted thoroughly with ethyl acetate
  7. washthe combined extracts were washed with 5% aqueous NaHCO3 and brine
  8. dry with materialdried over MgSO4
  9. customEvaporation of the solvent under vacuum
  10. customgave an oil which
  11. customevaporated under vacuum

Sources & evidence

ORD record
ord-104ee90c8a6c481f86e18cf1c07937ff
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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