Potassium Carbonate → HCID 18367733, compound

HRID 379827Notes

Reaction equation

HRID 379827 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4](C(OCC)=O)[C:3]=1[C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=1.C(=O)([O-])[O-:28].[K+].[K+].NC1C2C(=CC(Cl)=CC=2)NC=1C(=O)C1C=CC=C(C#N)C=1>C(O)C.O>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([NH2:25])=[O:28])[CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18367753HCID 18367753, compoundHCID 18367764HCID 18367764, compound

Product 1

HCID 18367733HCID 18367733, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-amino-6-chloro-2-(3-cyanobenzoyl)-1-(ethoxycarbonyl)indole (step 1, 10.4 g, 28 mmol) and potassium carbonate (20 g, 140 mmol) in ethanol (100 ml) and water (100 ml) was heated at reflux for 4 h. The mixture was cooled and concentrated, and the residue partitioned between water (100 ml) and ethyl acetate (250). The organic layer was dried (MgSO4) and concentrated. The residual oil was purified by flash column chromatography eluting with hexane/ethyl acetate (2/1) to give; 3-Amino-6-chloro-2-(3-cyanobenzoyl)indole (Example 127):

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customthe residue partitioned between water (100 ml) and ethyl acetate (250)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residual oil was purified by flash column chromatography
  9. washeluting with hexane/ethyl acetate (2/1)
  10. customto give

Sources & evidence

ORD record
ord-cc24634d2d104793aec9606402a2dddd
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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