Cesium carbonate → HCID 69742655, compound

HRID 351598Notes

Reaction equation

HRID 351598 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]>CN(C)C=O.C(OCC)(=O)C>[CH3:24][O:23][C:21]([C:20]1[CH2:19][N:10]2[CH:9]=[CH:8][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH:1]=1)[C:11]2=3)=[O:22]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 76934Methyl 3-bromopropanoateHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 69742655HCID 69742655, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-formylindole (30 g, 0.206 mol) in dimethylformamide (930 mL) was added cesium carbonate (148.2 g, 0.454 mol) and the mixture was stirred vigorously at room temperature for 30 min. Methyl 3-bromopropionate (51.6 g, 0.308 mol) was added and the reaction mixture was heated to 80° C. for 24 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered through a pad of Celite. The filtrate was washed with water and saturated aqueous sodium chloride, and the aqueous layers were back extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The crude product was passed through a short silica plug and concentrated under reduced pressure. Recrystallization of the crude product from chloroform and hexanes gave 4H-pyrrolo[3,2, 1-ij]quinoline-5-carboxylic acid methyl ester (17 g, 38.7% yield). Chromatography of the mother liquor gave additional 4H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid methyl ester (1.27 g, 2.9% yield) and 6H-Pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid methyl ester (0.51 g, 1.2% yield).

Workup

  1. temperaturethe reaction mixture was heated to 80° C. for 24 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through a pad of Celite
  4. washThe filtrate was washed with water and saturated aqueous sodium chloride
  5. extractionthe aqueous layers were back extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. concentrationconcentrated under reduced pressure
  9. customRecrystallization of the crude product from chloroform and hexanes

Sources & evidence

ORD record
ord-c46606aaa3ba4ea993101b192642c527
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Reaction notes

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