HCID 68711364, compound → HCID 58864447, compound

HRID 2355955Notes

Reaction equation

HRID 2355955 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]([NH:18]C(OCC1C=CC=CC=1)=O)=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[NH:11][CH:10]=[C:9]2[C:16]#[N:17]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH2:18])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[NH:11][CH:10]=[C:9]2[C:16]#[N:17]

Participants

4

Reactant 1

HCID 68711364HCID 68711364, compound

Product 1

HCID 58864447HCID 58864447, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Benzyloxycarbonylamino-3-(3-cyano-7-methyl-1H-indol-5-yl)-acrylic acid methyl ester (0.1 g, 0.26 mmol) in methanol (2.5 mL) was flushed with nitrogen, and treated with palladium on charcoal (10%, 10 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography gave 60 mg (90%) of the desired material. LC/MS: tR=0.93 min, 258.22 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-83e885975529434981bfb0463a7d6bc6
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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