Potassium Carbonate → HCID 18542226, compound

HRID 396553Notes

Reaction equation

HRID 396553 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[NH:7][C:6]=1[C:15]([C:17]1[N:18]([CH3:22])[CH:19]=[CH:20][CH:21]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>CO.O>[Cl:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:15]([C:17]1[N:18]([CH3:22])[CH:19]=[CH:20][CH:21]=1)=[O:16])=[C:5]2[CH2:4][C:3]([OH:23])=[O:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23003285HCID 23003285, compound

Product 1

HCID 18542226HCID 18542226, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of methyl[5-chloro-2-(1-methylpyrrole-2-carbonyl)-1H-indol-3-yl]acetate (Example 251, 250 mg, 0.79 mmol) and potassium carbonate (900 mg, 6.4 mmol) in methanol-water (1:1, 40 ml) was heated at reflux temperature for 1 h. After cooling to room temperature, the mixture was concentrated. The residue was neutralized with 2N aqueous HCl and extracted with ethyl acetate (50 ml×2) The combined extracts were dried (MgSO4) and concentrated. The residual solids were recrystallized from ethyl acetate/hexane to afford 40 mg (23%) of the title compound as pale yellow solids.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. concentrationthe mixture was concentrated
  4. extractionextracted with ethyl acetate (50 ml×2) The combined extracts
  5. dry with materialwere dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residual solids were recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d263960381824cd2af6c666b306a8949
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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