95426-76-9 → HCID 53899836, compound

HRID 1292380Notes

Reaction equation

HRID 1292380 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH2:21][NH2:22])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Br:23][C:24]1[CH:33]=[CH:32][C:27]([CH:28]=[CH:29][CH2:30]Br)=[CH:26][CH:25]=1>CN(C)C=O.C(Cl)Cl>[Br:23][C:24]1[CH:33]=[CH:32][C:27]([CH:28]=[CH:29][CH2:30][NH:22][CH2:21][CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 368016595426-76-9HCID 545198061-Bromo-4-(3-bromoprop-1-en-1-yl)benzene

Product 1

HCID 53899836HCID 53899836, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]ethylamine (261 mg in a mixture of 3 mL N,N-dimethylformamide and 8 mL methylene chloride) at 0° C. was added a solution of 81 mg of 4-bromocinnamyl bromide in 2 mL methylene chloride and the mixture allowed to warm to room temperature. After 27 hours the reaction was quenched by the addition of water followed by extraction with ethyl acetate. The organic portion was dried over over sodium sulfate and purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (93 mg). m/e=491 (M)

Workup

  1. customAfter 27 hours the reaction was quenched by the addition of water
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic portion was dried over over sodium sulfate
  4. custompurified by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-802c87a8721940b4ace74b8c3a201f94
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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