Cesium carbonate → HCID 118222818, compound

HRID 629176Notes

Reaction equation

HRID 629176 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2.[CH2:17](I)[CH2:18][CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:17][CH2:18][CH3:19])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 15365972Ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 118222818HCID 118222818, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate (103 mg, 0.47 mmol), propyl iodide (141 mg, 0.56 mmol) and cesium carbonate (230 mg, 0.70 mmol) in 1 mL dimethylformamide was stirred vigorously at 100° C. in a sealed vessel for 16 h. After cooling to room temperature, solids were filtered and the liquor concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (20-40% ethyl acetate in hexanes) to give ethyl 1-methyl-5-propoxy-1H-indole-2-carboxylate (96 mg, 55%). Used without further characterization.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationsolids were filtered
  3. concentrationthe liquor concentrated
  4. washThe crude residue was subjected to chromatography on silica gel with gradient elution (20-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5560c330d4be4ec984dad9b77918fbe6
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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