Ethyl Bromide → HCID 18705851, compound

HRID 2287849Notes

Reaction equation

HRID 2287849 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:18][C:8]2=[CH:9][C:10]3[C:11](=[O:17])[NH:12][C:13](=[O:16])[C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:2][CH3:3].C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[CH3:29]>CN(C=O)C>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:18][C:8]2=[CH:9][C:10]3[C:11](=[O:17])[N:12]([CH2:28][CH3:29])[C:13](=[O:16])[C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 18705862HCID 18705862, compound

Product 1

HCID 18705851HCID 18705851, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(dipropylamino)-6,7-dihydrocyclopent[f]isoindole-1,3(2H,5H)-dione (93, 0.15 g, 0.52 mmol) in DMF (10 mL) at 0° C. was added anhydrous K2CO3 (0.14 g, 1.04 mmol) followed by ethyl bromide (0.06 mL, 0.79 mmol). The reaction was stirred at 0° C. for 2 hr then allowed to warm to r.t. Continued stirring overnight then quenched with H2O. The solution was extracted with CH2Cl2 and the organic layers were washed with brine, dried (MgSO4), and concentrated. The residue was further concentrated on the high vac to remove any excess DMF and the resulting greenish solid was purified using silica gel, eluting with 3:1 hexane/acetone to give 95 as an off-white solid. The solid was converted to an HCl salt and recrystallized from hot MeOH/EtOAc to give 95 as a white solid (m.p. 225-230° C.).

Workup

  1. temperatureto warm to r.t
  2. stirringContinued stirring overnight
  3. customthen quenched with H2O
  4. extractionThe solution was extracted with CH2Cl2
  5. washthe organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. concentrationThe residue was further concentrated on the high vac
  9. customto remove any excess DMF
  10. customthe resulting greenish solid was purified
  11. washeluting with 3:1 hexane/acetone

Sources & evidence

ORD record
ord-9528f6c88f264c06b47faff310476749
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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