Cesium carbonate → ethyl 1-(4-methoxybutyl)-7-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

HRID 1184055Notes

Reaction equation

HRID 1184055 reaction equation
[O:1]=[C:2]1[C:10]2[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.CS(O[CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.O>[CH3:26][O:25][CH2:24][CH2:23][CH2:22][CH2:21][N:9]1[C:10]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=[C:8]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 848532Ethyl 7-oxo-1,4,5,6-tetrahydroindole-2-carboxylateHCID 116870064-Methoxybutyl methanesulfonate

Product 1

HCID 58355155ethyl 1-(4-methoxybutyl)-7-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylateYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of ethyl 7-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (207 mg), 4-methoxybutyl methanesulfonate (273 mg) and cesium carbonate (652 mg) in N,N-dimethylacetamide (10 ml) was stirred at 60° C. for 15 hr. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate (10 ml×2). The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (5:95-3:7) was concentrated under reduced pressure to give the object product (250 mg).

Workup

  1. extractionextracted with ethyl acetate (10 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (5:95-3:7)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-409c4f51f5724c9799bca2071fd10c94
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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