3',4',5'-Trimethoxyacetophenone → (E)-3-(6-Methoxyindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one

HRID 618114

Reaction equation

HRID 618114 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:16][O:17][C:18]1[CH:26]=[C:25]2[C:21]([C:22]([CH:27]=O)=[CH:23][NH:24]2)=[CH:20][CH:19]=1>>[CH3:16][O:17][C:18]1[CH:26]=[C:25]2[C:21]([C:22](/[CH:27]=[CH:14]/[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:15])=[CH:23][NH:24]2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 9072146-Methoxy-1H-indole-3-carboxaldehyde

Product 1

HCID 21850283(E)-3-(6-Methoxyindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-oneYield 32%

Procedure

Substantially the same procedure as in Example 1 was repeated using 3',4',5'-trimethoxyacetophenone (659 mg) and 6-methoxyindole-3-carboxaldehyde (550 mg) except that the reaction solution was concentrated under reduced pressure, that the residue was purified by silica gel column chromatography, and that the obtained crude crystals were recrystallized from ethanol, to give Compound 39 (369 mg).

Workup

  1. concentrationwas concentrated under reduced pressure, that the residue
  2. customwas purified by silica gel column chromatography
  3. customthat the obtained crude crystals
  4. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-f3c262c37ecd43e0955d3e99bad2ecf7
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Linked notes

Loading…