3,5-Dimethyl-1H-pyrrole-2-carbaldehyde → Semaxinib

HRID 482035Notes

Reaction equation

HRID 482035 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][C:12]1[CH:16]=[C:15]([CH3:17])[NH:14][C:13]=1[CH:18]=O>N1CCCCC1.C(O)C>[CH3:17][C:15]1[NH:14][C:13]([CH:18]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[C:12]([CH3:11])[CH:16]=1

Participants

5

Reactant 2

HCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehydeHCID 321710Oxindole

Product 1

HCID 123015SemaxinibYield 57%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 134.0 mg of oxindole, 147.8 mg of the 3,5-dimethylpyrrole-2-carboxaldehyde, and 3 drops of piperidine in 2 mL of ethanol was stirred at 90° C. for 3 h. After cooling, the precipitate was filtered, washed with cold ethanol, and dried to yield 136.7 mg (57%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washwashed with cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-545a6866a99744e2b14c93bd883a168c
Source dataset
uspto-grants-1998_08
Patent number
US05792783

Reaction notes

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