Ethanol → HCID 86759609, compound

HRID 983120Notes

Reaction equation

HRID 983120 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.[N:18]1([CH2:23][CH2:24][NH:25][C:26]([C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][C:29]=2[CH:34]=O)=[O:27])[CH:22]=[CH:21][N:20]=[N:19]1.[CH2:36](O)C>N1CCCCC1>[N:18]1([CH2:23][CH2:24][NH:25][C:26]([C:28]2[CH:32]=[C:31]([CH2:33][CH3:36])[NH:30][C:29]=2[CH:34]=[C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[CH:16][C:8]=3[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[NH:12][C:11]2=[O:17])=[O:27])[CH:22]=[CH:21][N:20]=[N:19]1

Participants

5

Reactant 3

HCID 702EthanolHCID 207616192-formyl-5-methyl-1H-pyrrole-3 carboxylic acid (2-[1,2,3]triazol-1-yl-ethyl)-amideHCID 225618494-(3-Bromo-phenyl)1,3-dihydro-indol-2-one

Product 1

HCID 86759609HCID 86759609, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

To a solution of 4-(3-bromo-phenyl)-1,3-dihydro-indol-2-one (72 mg, 0.25 mmol) and 2-formyl-5-methyl-1H-pyrrole-3-carboxylic acid (2-[1,2,3]triazol-1-yl-ethyl)amide (64.8 mg, 0.25 mmol) in ethanol (2 mL) was added piperidine (3 drops). The reaction mixture was stirred at room temperature for three days. A yellow solid product was precipitated out, filtered, washed by ethanol for three times, and dried under high vacuum to provide pure product 2-[4-(3-bromo-phenyl)2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-5-ethyl-1H-pyrrole-3-carboxylic acid (2-[1,2,3]triazol-1-yl-ethyl)-amide as a yellow solid (96 mg, 74%).

Workup

  1. customA yellow solid product was precipitated out
  2. filtrationfiltered
  3. washwashed by ethanol for three times
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-7961005e801044d6ac1abd34f0e1785a
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

Loading…