Piperidine → 5-Ureido-3-[(4-bromopyrrol-2-yl)methylene]indolin-2-one

HRID 2213684Notes

Reaction equation

HRID 2213684 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)[C:2]([NH2:4])=[O:3].[Br:15][C:16]1[CH:17]=[C:18]([CH:21]=O)[NH:19][CH:20]=1.N1CCCCC1>C(O)C>[NH:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2=[CH:21][C:18]1[NH:19][CH:20]=[C:16]([Br:15])[CH:17]=1)[C:2]([NH2:4])=[O:3]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5996274-Bromo-1H-pyrrole-2-carbaldehydeHCID 219578045-Ureidoindolin-2-one

Product 1

HCID 695454445-Ureido-3-[(4-bromopyrrol-2-yl)methylene]indolin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution 5-ureidoindolin-2-one (326 mg, 1.71 mmol) in ethanol was added 4-bromo-2-pyrrolecarboxaldehyde (297 mg, 1.71 mmol), and piperidine (0.2 mL). The reaction mixture was refluxed for 18 hours. The mixture was cooled and filtered to afford a golden-colored solid which was washed with ethanol and ether to afford 5-ureido-3-[(4-bromopyrrol-2-yl)methylene]indolin-2-one; (453 mg); 1H NMR (400 MHz, DMSO-d6) δ 5.77 (s, 2H); 6.74–6.76 (d, 1H); 6.96 (s, 1H); 7.02–7.04 (dd, 1H); 7.41–7.42 (m, 1H); 7.52–7.53 (m, 1H); 7.73–7.74 (d, 1H); 8.34 (s, 1H); 10.82 (bd, 1H); 13.5 (bs, 1H) ppm.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customto afford a golden-colored solid which
  5. washwas washed with ethanol and ether

Sources & evidence

ORD record
ord-f6e43e8e7e374bf2853fffa7b5147235
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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