Potassium Carbonate → HCID 11631327, compound

HRID 1020311Notes

Reaction equation

HRID 1020311 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(NC(=O)[O-])C.[OH:22][C:23]1[C:24]([Cl:36])=[CH:25][C:26]2[CH:27]([CH3:35])[CH:28]3[CH2:32][NH:31][CH2:30][CH:29]3[C:33]=2[CH:34]=1>C(#N)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:22][C:23]2[C:24]([Cl:36])=[CH:25][C:26]3[CH:27]([CH3:35])[CH:28]4[CH2:32][NH:31][CH2:30][CH:29]4[C:33]=3[CH:34]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 86602845N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 11631327HCID 11631327, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

4-Fluorobenzyl bromide (23 μL, 0.19 mmol) and potassium carbonate (100 mg, 0.78 mmol) were added to a solution of N-ethylcarbamate-5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 5, Step A) (46 mg, 0.16 mmol) in acetonitrile (3 mL), and stirred overnight at 80° C. The reaction was cooled to room temperature, concentrated by rotary evaporation and taken up in H2O (5 mL). The product was extracted with EtOAc (3×10 mL). The combined organic extracts were dried over MgSO4 and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C22H23ClFNO3+H: 404, observed: 404.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated by rotary evaporation
  3. extractionThe product was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5f8838eb9f30447184fbde89d1cdadfa
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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