HCID 67176177, compound → HCID 58305666, compound

HRID 2362205Notes

Reaction equation

HRID 2362205 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]([CH3:21])[CH:4]=1)#[N:2]>C(O)C.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]([CH3:21])[CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 67176177HCID 67176177, compound

Product 1

HCID 58305666HCID 58305666, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-(1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)acrylate (6C) (8.0 g, 28.6 mmol) in ethanol was added 10% Pd/C (0.8 g). The mixture was stirred under 1 atm of H2 for 30 min at room temperature and filtrated. The resultant filtrate was concentrated to dryness affording the crude product of ethyl 3-(1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (7.5 g), which was used for the next step without further purification: LC-MS m/z 283.0 [M+H]+, purity 68%.

Workup

  1. filtrationfiltrated
  2. concentrationThe resultant filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-d55b2e3b083d4a64b77801a3c102b0f5
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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