Water → 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-furanyl)acetamide

HRID 353474Notes

Reaction equation

HRID 353474 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16](=[O:20])[C:17](Cl)=[O:18])=[CH:8]2)=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH2:28][O:27][C:26](=[O:29])[CH:25]=1.O>O1CCCC1>[O:29]=[C:26]1[O:27][CH2:28][C:24]([NH:23][C:17](=[O:18])[C:16]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([CH2:6][C:5]3[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:8]=2)=[O:20])=[CH:25]1

Participants

5

Reactant 3

HCID 962WaterHCID 109804772-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxo-acetyl chlorideHCID 133748614-amino-5H-furan-2-one

Product 1

HCID 101574932-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-furanyl)acetamideYield 50.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxo-acetyl chloride (0.45 g) and 4-amino-5H-furan-2-one (0.30 g) in dry tetrahydrofuran (10 ml) is refluxed for 2 h. After cooling at room temperature, the reaction mixture is poured into water (200 ml) and the resulting suspension is left under stirring for 1 h. The solid is filtered off and resuspended in methanol (4.3 ml) under stirring for 1 h, then collected by filtration to give N-(5-oxo-2,5-dihydrofuran-3-yl)-2-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxo-acetamide (0.27 g).

Workup

  1. waitthe resulting suspension is left
  2. filtrationThe solid is filtered off
  3. stirringunder stirring for 1 h
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-32fcb394c3cf44509a628c01ecb53166
Source dataset
uspto-grants-2004_06
Patent number
US06753342B2

Reaction notes

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