Piperidine → 5-Cyano-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one

HRID 2213679Notes

Reaction equation

HRID 2213679 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)#[N:2].[C:13]([C:16]1[NH:17][CH:18]=[CH:19][CH:20]=1)(=O)[CH3:14].N1CCCCC1>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[C:13]([C:16]1[NH:17][CH:18]=[CH:19][CH:20]=1)[CH3:14])#[N:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 140792-AcetylpyrroleHCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrile

Product 1

HCID 695452315-Cyano-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-cyanoindolin-2-one (158 mg, 1 mmol) in ethanol (15 mL) was added 2-acetylpyrrole (95 mg, 1 mmol) and piperidine (0.1 mL). The reaction mixture was refluxed for 2 hours. A golden-colored product precipitated from the reaction mixture, which was filtered and washed with ethanol to afford 5-cyano-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one; (160 mg) 1H NMR (400 MHz, DMSO-d6) δ 2.80 (s, 3H), 6.40. (m, 1H), 7.04 (d, 1H), 7.20 (m, 1H), 7.42 (m, 1H), 7.60 (dd, 1H), 8.04 (s, 1H), 11.40 (s, 1H) ppm.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. customA golden-colored product precipitated from the reaction mixture, which
  3. filtrationwas filtered
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-b24a7961fea84a1cbb0f94b2e807fcc6
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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