4-(4-Fluoro-phenyl)-1,3-dihydro-indol-2-one → 2-[4-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-5-methyl-1 H-pyrrole-3-carboxylic acid (3-pyrrolidin-1-yl-propyl)-amide

HRID 983140Notes

Reaction equation

HRID 983140 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[N:18]1([CH2:23][CH2:24][CH2:25][NH:26][C:27]([C:29]2[CH:33]=[C:32]([CH3:34])[NH:31][C:30]=2[CH:35]=O)=[O:28])[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C.N1CCCCC1>[N:18]1([CH2:23][CH2:24][CH2:25][NH:26][C:27]([C:29]2[CH:33]=[C:32]([CH3:34])[NH:31][C:30]=2[CH:35]=[C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[CH:16][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[NH:12][C:11]2=[O:17])=[O:28])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 225618524-(4-Fluoro-phenyl)-1,3-dihydro-indol-2-oneHCID 865876602-formyl-5-methyl-1H-pyrrole-3-carboxylic acid (3-pyrrolidin-1-yl-propyl)-amide

Product 1

HCID 726376662-[4-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-5-methyl-1 H-pyrrole-3-carboxylic acid (3-pyrrolidin-1-yl-propyl)-amideYield 79%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4-fluoro-phenyl)-1,3-dihydro-indol-2-one (56.8 mg, 0.25 mmol) and 2-formyl-5-methyl-1H-pyrrole-3-carboxylic acid (3-pyrrolidin-1-yl-propyl)-amide (68.5 mg, 0.26 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-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid (3-pyrrolidin-1-yl-propyl)amide as a yellow solid (93.2 mg, 79%).

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-ce5576d6876d4e7f9959cdb8cdb8f7ce
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

Loading…