HCID 58056458, compound → HCID 58056503, compound

HRID 555669Notes

Reaction equation

HRID 555669 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]([Cl:15])[CH:13]=2)[NH:8][CH:7]=1.[H][H]>[Pd].C(OCC)(=O)C>[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]([Cl:15])[CH:13]=2)[NH:8][CH:7]=1

Participants

5

Reactant 2

HCID 58056458HCID 58056458, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 58056503HCID 58056503, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a flask, (E)-3-(5-chloro-1H-indol-3-yl)-acrylic acid methyl ester (8, 3.4 g, 0.014 mol) and 10% palladium on carbon were combined and 140 mL of ethyl acetate was added. Vacuum was applied and the flask was back filled with hydrogen, repeated application of vacuum and hydrogen back fill for total of three times. The reaction was capped with a hydrogen filled balloon and the reaction stirred overnight at room temperature. TLC (20% ethyl acetatethexane) indicated absence of starting material and a major new spot. The reaction was filtered through celite and the filter rinsed generously with a total of 250 mL of ethyl acetate. The yellow filtrate solution was roto-evaporated to near dryness, silica was added, and the solvent fully removed. Column chromatography was performed, eluting with 2 to 30% ethyl acetate/hexane, then flushing with 40% ethyl acetate/hexane to provide the desired compound. 1H NMR consistent with structure.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washthe filter rinsed generously with a total of 250 mL of ethyl acetate
  3. customThe yellow filtrate solution was roto-evaporated
  4. additionwas added
  5. customthe solvent fully removed
  6. washeluting with 2 to 30% ethyl acetate/hexane
  7. customflushing with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-61a2d29cc5324867a33ea5a7a826ac60
Source dataset
uspto-grants-2011_11
Patent number
US08053463B2

Reaction notes

Loading…