Pyrrole-2-carboxaldehyde → HCID 69844601, compound

HRID 1860267Notes

Reaction equation

HRID 1860267 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][C:7]1[S:15][C:10]2[NH:11][C:12](=[O:14])[CH2:13][C:9]=2[CH:8]=1)[CH3:2].[NH:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH:22]=O>N1CCCCC1.CC(O)C>[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[CH:6]\[C:7]1[S:15][C:10]2[NH:11][C:12](=[O:14])[C:13](=[CH:22][C:18]3[NH:17][CH:21]=[CH:20][CH:19]=3)[C:9]=2[CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 69844669HCID 69844669, compound

Product 1

HCID 69844601HCID 69844601, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8082PiperidineSolvent

Conditions

Temperature
75 °C

Procedure

3-(5-Oxo-5,6-dihydro-4H-thieno[2,3-b]pyrrol-2-yl)-acrylic acid ethyl ester (30 mg, 0.13 mmol) was dissolved in a solution of 1% piperidine in 2-propanol (1 ml). Pyrrole-2-carboxaldehyde (0.15 mmol, 14 mg) was added in one portion and the mixture heated at 75° C. for 30 minutes. The reaction mixture was poured into an ice/water mixture (4 ml) and the precipitated solid was collected by filtration and washed with water to give 10 mg of (Z)-3-[5-Oxo-4-(1H-pyrrol-2-ylmethylene)-5,6-dihydro-4H-thieno[2,3-b]pyrrol-2-yl]-acrylic acid ethyl ester as a red solid. MS(ES): mle 315 [M+H].

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-397fffade79040a09908cf4973aa68b8
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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