Potassium Carbonate → HCID 69270198, compound

HRID 751520Notes

Reaction equation

HRID 751520 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]2[C:12](=[O:28])[N:13]([CH3:27])[C:14](=[O:26])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH3:25])[CH:17]=2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][CH2:37][O:38]C1CCCCO1>CN(C)C=O.C(OCC)(=O)C>[OH:38][CH2:37][CH2:36][O:1][C:2]1[CH:3]=[C:4]([C:11]2[C:12](=[O:28])[N:13]([CH3:27])[C:14](=[O:26])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH3:25])[CH:17]=2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 69269051HCID 69269051, compound

Product 1

HCID 69270198HCID 69270198, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Add to a mixture of 3-(5-hydroxybenzofur-7-yl)-1-methyl-4-(1-methyl-1H-indol-3-yl)pyrrole-2,5-dione (2.5 g, 6.7 mmol) and potassium carbonate (2.78 g, 20.1 mmol) in N,N-dimethylformamide (40 ml), 2-(2-bromoethoxy)tetrahydropyran (3.04 ml, 20.1 mmol). Heat the mixture to 80° C. under nitrogen atmosphere for overnight. Diluted with ethyl acetate, wash with water, brine, dry over magnesium sulfate, filter and concentrate to red solid. Dissolve the solid in methanol (40 ml), add p-toluenesulfonic acid (3 g), stir for 20 minutes. Diluted with ethyl acetate, wash with water, brine, dry over magnesium sulfate, filter and concentrate to afford the title compound (1.88 g, 67%) as a red solid. HRMS: calculated 417.1450 found 417.1462.

Workup

  1. washwash with water, brine
  2. dry with materialdry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate to red solid
  5. dissolutionDissolve the solid in methanol (40 ml)
  6. additionadd p-toluenesulfonic acid (3 g)
  7. additionDiluted with ethyl acetate
  8. washwash with water, brine
  9. dry with materialdry over magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate

Sources & evidence

ORD record
ord-8da82bca18b8441a903079ac3c529bd4
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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