6-Thiophen-2-yl-1,3-dihydro-indol-2-one → 3-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-6-thiophen-2-yl-1,3-dihydro-indol-2-one

HRID 2120202Notes

Reaction equation

HRID 2120202 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][C:11](=[O:15])[NH:12]2)=[CH:8][CH:7]=1.[CH3:16][N:17]([CH3:30])[CH2:18][CH2:19][CH2:20][C:21]1[C:22]([CH3:29])=[C:23]([CH:27]=O)[NH:24][C:25]=1[CH3:26]>N1CCCCC1.C(O)C>[CH3:30][N:17]([CH3:16])[CH2:18][CH2:19][CH2:20][C:21]1[C:22]([CH3:29])=[C:23]([CH:27]=[C:10]2[C:9]3[C:13](=[CH:14][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[CH:7][CH:8]=3)[NH:12][C:11]2=[O:15])[NH:24][C:25]=1[CH3:26]

Participants

5

Reactant 2

HCID 219069896-Thiophen-2-yl-1,3-dihydro-indol-2-oneHCID 219257584-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 544131473-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-6-thiophen-2-yl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-thiophen-2-yl-1,3-dihydroindol-2-one (100 mg, 0.46 mmol), 4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrole-2-carboxaldehyde (100 mg, 0.48 mmol), and piperidine (1 drop) in ethanol (2 mL) was stirred at reflux overnight. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 3-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-6-thiophen-2-yl-1,3-dihydro-indol-2-one.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-b5af273db04e462d9484b5431486ad31
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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