Diethylamine → HCID 69269884, compound

HRID 751522Notes

Reaction equation

HRID 751522 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:14]2[C:15](=[O:31])[N:16]([CH3:30])[C:17](=[O:29])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH3:28])[CH:20]=2)[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[CH:13]=1.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33]>CN1CCCC1.C(OCC)(=O)C>[CH2:32]([N:34]([CH2:35][CH3:36])[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:14]2[C:15](=[O:31])[N:16]([CH3:30])[C:17](=[O:29])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH3:28])[CH:20]=2)[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[CH:13]=1)[CH3:33]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 69271647HCID 69271647, compound

Product 1

HCID 69269884HCID 69269884, compound

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add to a solution of 3-[5-(2-bromoethoxy)benzofur-7-yl]-1-methyl-4-(1-methyl-1H-indol-3-yl)pyrrole-2,5-dione (600 mg, 1.25 mmol) in 1-methylpyrrolidine (8 ml), diethylamine (0.65 ml, 6.28 mmol). Stir overnight under nitrogen atmosphere. Heat the reaction to 60° C. for 4 hours. Dilute with ethyl acetate, wash with water, brine, dry over magnesium sulfate, filter and concentrate to red oil. Flash chromatography through SCX column affords the title compound as a red oil. MS(ES+): 472.1; HRMS: calculated 472.2236 found 472.2235.

Workup

  1. temperatureHeat
  2. customthe reaction to 60° C. for 4 hours
  3. washwash with water, brine
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate to red oil

Sources & evidence

ORD record
ord-0d2a0179cb9c4c5e8b7bed56952924f0
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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