Diisopropylethylamine → 3-[1-(Benzenesulphonyl)-3-pyrrolyl]-4-(1-methyl-3-indolyl)furan-2,5-dione

HRID 345700Notes

Reaction equation

HRID 345700 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19]([N:22]([CH:25]([CH3:27])[CH3:26])[CH2:23][CH3:24])(C)C>ClCCl>[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]3[C:16](=[O:18])[O:17][C:16](=[O:17])[C:15]=3[C:24]3[C:27]4[C:25](=[CH:26][CH:2]=[CH:1][CH:6]=4)[N:22]([CH3:19])[CH:23]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 13157056(1-Benzenesulfonyl-1H-pyrrol-3-yl)-acetic acid

Product 1

HCID 151137143-[1-(Benzenesulphonyl)-3-pyrrolyl]-4-(1-methyl-3-indolyl)furan-2,5-dioneYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1 g of 1-(benzenesulphonyl)-3-pyrrolylacetic acid in 25 ml of dichloromethane was treated at 0° C. with a solution of 837 mg of 1-methylindole-3-glyoxylyl chloride in 25 ml of dichloromethane and then with 975 mg of diisopropylethylamine. The mixture was allowed to warm to room temperature and was then stirred for 22 hours. After concentration and chromatography of the residue on silica gel with ethyl acetate/hexane (1:1) there were obtained 540 mg of 3-[1-(benzenesulphonyl)-3-pyrrolyl]-4-(1-methyl-3-indolyl)furan-2,5-dione.

Workup

  1. concentrationAfter concentration and chromatography of the residue on silica gel with ethyl acetate/hexane (1:1) there

Sources & evidence

ORD record
ord-cedf31ab25d440da81a3f6afede9ef71
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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