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

HRID 618115Notes

Reaction equation

HRID 618115 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].[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([CH:26]=O)=[CH:22][NH:23]2)=[CH:19][CH:18]=1>>[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21](/[CH:26]=[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:22][NH:23]2)=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 126146696-Chloro-1H-indole-3-carboxaldehyde

Product 1

HCID 21850251(E)-3-(6-Chloroindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-oneYield 69.2%

Procedure

Substantially the same procedure as in Example 1 was repeated using 3',4',5'-trimethoxyacetophenone (2.1 g) and 6-chloroindole-3-carboxaldehyde (1.8 g) except that the obtained product was recrystallized from ethyl acetate, to give Compound 42 (2.57 g).

Workup

  1. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-dbec2b02c2eb4bf0b7f109ff3d2ef1a6
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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