Hydrochloric Acid → 3-bromo-4-(1H-indol-3-yl)-1-methyl-pyrrole-2,5-dione

HRID 859126

Reaktionsgleichung

Reaktionsgleichung von HRID 859126
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:20][N:21]1[C:25](=[O:26])[C:24](Br)=[C:23]([Br:28])[C:22]1=[O:29].Cl>O1CCCC1>[Br:28][C:23]1[C:22](=[O:29])[N:21]([CH3:20])[C:25](=[O:26])[C:24]=1[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 798IndoleHCID 181552,3-Dibromo-N-methylmaleimideHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 97965023-bromo-4-(1H-indol-3-yl)-1-methyl-pyrrole-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1.445 g of indole dissolved in 29 ml of dry tetrahydrofliran is brought to from −20 to −10° C. under argon, and then 26 ml of LiHMDS (1M in hexane) are added dropwise in the course of 15 minutes. After 45 minutes at −10° C., the solution is diluted with an additional 15 ml of tetrahydrofuran and a solution of 2 g of N-methyl-2,3-dibromomaleimide dissolved in 17 ml of tetrahydrofuran is added dropwise in the course of 30 minutes. After 15 minutes at −10° C. and 15 minutes at 0° C., the reaction is stopped by the addition, at 0° C., of 50 ml of a 0.3N hydrochloric acid solution. The reaction mixture is extracted with ethyl acetate, and the organic phases are washed with a saturated NaCl solution, dried over MgSO4 and then evaporated under reduced pressure. The desired product is precipitated using methanol.

Aufarbeitung

  1. customis brought to from −20 to −10° C. under argon
  2. additionis added dropwise in the course of 30 minutes
  3. waitAfter 15 minutes at −10° C.
  4. extractionThe reaction mixture is extracted with ethyl acetate
  5. washthe organic phases are washed with a saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe desired product is precipitated

Quellen und Nachweise

ORD-Eintrag
ord-8d71644fca2846b59ac06d95e5ee4419
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151108B2

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