4-(4-Fluoro-phenyl)-1,3-dihydro-indol-2-one → HCID 69741040, compound

HRID 1839683Notes

Reaction equation

HRID 1839683 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.[CH3:18][C:19]1[NH:23][C:22]([CH:24]=O)=[C:21]([C:26]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[O:27])[CH:20]=1>C(O)C.N1CCCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[C:10](=[CH:24][C:22]2[NH:23][C:19]([CH3:18])=[CH:20][C:21]=2[C:26]([N:28]2[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]2)=[O:27])[C:11](=[O:17])[NH:12]3)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 225618524-(4-Fluoro-phenyl)-1,3-dihydro-indol-2-oneHCID 22561955HCID 22561955, compound

Product 1

HCID 69741040HCID 69741040, compoundYield 40%

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 5-methyl-3-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde (61.2 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 4-(4-fluoro-phenyl)-3-[5-methyl-3-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-1,3-dihydro-indol-2-one as a yellow solid (44.1 mg, 40%).

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-d17a6aa6829d4450ac4a37dde159b73a
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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