Cesium carbonate → 5-(3-Dimethylamino-piperidine-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

HRID 2241714Notes

Reaction equation

HRID 2241714 reaction equation
[CH3:1][N:2]([CH3:25])[CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]3)=[O:10])[CH2:4]1.[CH:26](CS([O-])(=O)=O)([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:23]([O:22][C:20]([C:15]1[N:16]([CH:26]([CH3:28])[CH3:27])[C:17]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:9]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([N:2]([CH3:25])[CH3:1])[CH2:4]1)=[O:10])=[CH:19][CH:18]=2)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 22141912Isopropyl-methanesulfonateHCID 68680571Ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate

Product 1

HCID 686800365-(3-Dimethylamino-piperidine-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate (1.51 g, 4 mmol) in acetonitrile (30 ml) were added isopropylmethane-sulfonate (1.8 eq, 1.1 g) and caesium carbonate (1.8 eq, 2.6 g). The mixture was heated overnight at reflux. The solvent was evaporated under reduced pressure and the residue partitioned between water and tert-butylmethyl ether. The phases were separated, the aqueous phase extracted with tert-butylmethyl ether and the combined organic phases washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (4:1 chloroform/methanol eluant) to afford the product as a light-brown gum. (31%)

Workup

  1. temperatureThe mixture was heated overnight
  2. temperatureat reflux
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between water and tert-butylmethyl ether
  5. customThe phases were separated
  6. extractionthe aqueous phase extracted with tert-butylmethyl ether
  7. washthe combined organic phases washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (4:1 chloroform/methanol eluant)

Sources & evidence

ORD record
ord-973c0d99ac7342b285f6209f6c61ce2d
Source dataset
uspto-grants-2010_05
Patent number
US07723325B2

Reaction notes

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