HCID 58056437, compound → HCID 58056522, compound

HRID 555666Notes

Reaction equation

HRID 555666 reaction equation
[CH3:1][O:2][C:3](=[O:16])/[CH:4]=[CH:5]/[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][CH:7]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][CH:7]=1

Participants

4

Reactant 1

HCID 58056437HCID 58056437, compound

Product 1

HCID 58056522HCID 58056522, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a flask, (E)-3-(5-fluoro-1H-indol-3-yl)-acrylic acid methyl ester (2, 530.00 mg, 0.0024178 mol) was dissolved in 14.69 mL methanol. Palladium (10% on activated carbon, 25.73 mg, 0.0002418 mol) was added and the reaction was stirred under an atmosphere of hydrogen overnight. TLC analysis showed complete conversion to a new product. The mixture was filtered and concentrated under reduced pressure to provide the desired compound (3, 500 mg, 93.4%). 1H NMR consistent with desired compound. MS(ESI) [M+H+]+=222.0.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ec27bc002b44b7aab98d8ade185e382
Source dataset
uspto-grants-2011_11
Patent number
US08053463B2

Reaction notes

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