4-Pyridineacetic acid hydrochloride → 3-(1-Methyl-3-indolyl)-4-(4-pyridyl)furan-2,5-dione

HRID 1421185Notes

Reaction equation

HRID 1421185 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH:12]([N:15]([CH:18]([CH3:20])[CH3:19])[CH2:16][CH3:17])(C)C>ClCCl>[CH3:12][N:15]1[C:18]2[C:20](=[CH:3][CH:4]=[CH:5][CH:19]=2)[C:17]([C:8]2[C:9](=[O:10])[O:10][C:9](=[O:11])[C:8]=2[C:5]2[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=2)=[CH:16]1

Participants

4

Reactant 2

HCID 810974-Pyridineacetic acid hydrochlorideHCID 81531Diisopropylethylamine2×

Product 1

HCID 187802473-(1-Methyl-3-indolyl)-4-(4-pyridyl)furan-2,5-dioneYield 21.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 g of 4-pyridyl-acetic acid hydrochloride and 3.72 g of diisopropylethylamine in 50 ml of dichloromethane were treated at 0° C. firstly with 6.37 g of 1-methylindole-3-glyoxylyl chloride in 50 ml of dichloromethane and then with 7.5 g of diisopropylethylamine. The mixture was allowed to warm to room temperature and was then stirred for 65 hours. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane and chromatographed on silica gel with ethyl acetate. The product-containing fractions were concentrated. Crystallization from ethyl acetate/hexane yielded 940 mg of 3-(1-methyl-3-indolyl)-4-(4-pyridyl)furan-2,5-dione, m.p. 217°-219° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customchromatographed on silica gel with ethyl acetate
  3. concentrationThe product-containing fractions were concentrated
  4. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ea42e61ee9384f8b81cdccc16c9cee75
Source dataset
uspto-grants-2000_06
Patent number
USRE036736

Reaction notes

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