Indole → HCID 12047551, compound

HRID 890997Notes

Reaction equation

HRID 890997 reaction equation
[Mg:1].Br[CH2:3][CH3:4].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[CH2:14]([O:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]([Br:29])=[C:25]([Br:30])[C:24]1=[O:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([Mg:1][Br:29])[CH3:4].[CH2:14]([O:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]([C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:5][CH:6]=2)=[C:25]([Br:30])[C:24]1=[O:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 798IndoleHCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11122331N-benzyloxymethyl-2,3-dibromomaleimide

Product 2

HCID 12047551HCID 12047551, compoundHCID 178418443HCID 178418443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of ethylmagnesium bromide is prepared, starting from magnesium (6.75 mmol) suspended in bromoethane (6.75 mmol) and dry tetrahydrofuran (5 ml). The solution is stirred at ambient temperature for 15 minutes and is then heated at 40° C. for 20 minutes. A solution of indole (6.75 mmol) in 40 ml of dry tetrahydrofuran is then added dropwise. After stirring for 1 hour at 40° C., the reaction mixture is cooled and then a solution of N-benzyloxymethyl-2,3-dibromomaleimide (3.38 mmol) in 40 ml of dry tetrahydrofuran is added dropwise. The reaction mixture is stirred for 15 hours and is then hydrolysed with saturated aqueous ammonium chloride solution. The organic product is extracted with ethyl acetate, and the organic phases are then combined, dried over magnesium sulphate and filtered. After evaporating off the solvent and purifng the residue by chromatography on silica gel (cyclohexane/ethyl acetate: 4/1), the expected product is isolated.

Workup

  1. temperatureis then heated at 40° C. for 20 minutes
  2. stirringAfter stirring for 1 hour at 40° C.
  3. temperaturethe reaction mixture is cooled
  4. stirringThe reaction mixture is stirred for 15 hours
  5. extractionThe organic product is extracted with ethyl acetate
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customAfter evaporating off the solvent

Sources & evidence

ORD record
ord-d4f910cff7604c6c9ed03c88161f5350
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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