HCID 68709329, compound → HCID 58864501, compound

HRID 2355950Notes

Reaction equation

HRID 2355950 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]([NH:17]C(OCC1C=CC=CC=1)=O)=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[C:15]#[N:16]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH:4]([NH2:17])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[C:15]#[N:16]

Participants

4

Reactant 1

HCID 68709329HCID 68709329, compound

Product 1

HCID 58864501HCID 58864501, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Benzyloxycarbonylamino-3-(3-cyano-1H-indol-5-yl)-acrylic acid methyl ester (0.5 g, 1.3 mmol) in methanol (8 mL) was flushed with nitrogen, and treated with palladium on charcoal (10%, 50 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 0.3 g (92%) of the desired material. LC/MS: tR=0.80 min, 244.20 (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-cccc9ba8c9984956afc04a7f4eb0009d
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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