5-Methoxyindole → HCID 14855721, compound

HRID 440169Notes

Reaction equation

HRID 440169 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.Br[C:17]1[C:22](=[O:23])[NH:21][C:19](=[O:20])[C:18]=1Br.[Cl-].[NH4+:26].[C:27]1([CH3:33])[CH:32]=[CH:31]C=[CH:29][CH:28]=1.[CH2:34]([OH:36])C>O1CCCC1.C1(C)C=CC=CC=1>[CH3:34][O:36][C:29]1[CH:28]=[C:27]2[C:33](=[CH:1][CH:2]=1)[NH:26][CH:31]=[C:32]2[C:18]1[C:19]([NH:21][C:22](=[O:23])[C:17]=1[C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([O:6][CH3:5])[CH:8]=2)[NH:12][CH:11]=1)=[O:20]

Participants

8

Reactant 5

HCID 138725-MethoxyindoleHCID 14279DibromomaleimideHCID 25517Ammonium ChlorideHCID 21863594Toluene ethanolHCID 178418443HCID 178418443, compound

Product 1

HCID 14855721HCID 14855721, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 22 mmol ethyl magnesium bromide in 30 ml tetrahydrofuran is mixed at ambient temperature with a solution of 2.8 g (19 mmol) 5-methoxyindole in 50 ml toluene and stirred for 1 hour at ambient temperature. Under an atmosphere of nitrogen, there is then added dropwise thereto a solution of 1.5 g (5.8 mmol) dibromomaleinimide in 20 ml tetrahydrofuran/50 ml toluene and heated under reflux for 20 hours. After cooling, the reaction mixture is decomposed with a saturated aqueous solution of ammonium chloride, the products are extracted with ethyl acetate and the organic phase is dried over anhydrous sodium sulphate. After evaporation, the red residue obtained is triturated with a little methanol and the precipitated red product is filtered off with suction and dried in a vacuum at 0.1 Torr and 100° C. There is obtained 0.9 g (36% of theory) of red crystals; m.p. 336° C. (decomp.); RF=0.30 (toluene/ethanol 10:2 v/v).

Workup

  1. additionUnder an atmosphere of nitrogen, there is then added dropwise
  2. temperatureunder reflux for 20 hours
  3. temperatureAfter cooling
  4. extractionthe products are extracted with ethyl acetate
  5. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  6. customAfter evaporation
  7. customthe red residue obtained
  8. customis triturated with a little methanol
  9. filtrationthe precipitated red product is filtered off with suction
  10. customdried in a vacuum at 0.1 Torr and 100° C
  11. customThere is obtained 0.9 g (36% of theory) of red crystals

Sources & evidence

ORD record
ord-cf1fc428ce5542b0b689897172012740
Source dataset
uspto-grants-1996_05
Patent number
US05516915

Reaction notes

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