Sulfuric Acid → 4-(2-Amino)ethyloxy-9-benzyl-2-methoxycarbazole-5-carboxamide

HRID 51341

Reaktionsgleichung

Reaktionsgleichung von HRID 51341
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.OS(O)(=O)=O.[CH2:17]([N:24]1[C:36]2[CH:35]=[C:34]([O:37][CH3:38])[CH:33]=[C:32]([O:39][CH2:40][C:41]#[N:42])[C:31]=2[C:30]2[C:29]([C:43]([NH2:45])=[O:44])=[CH:28][CH:27]=[CH:26][C:25]1=2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[NH2:42][CH2:41][CH2:40][O:39][C:32]1[C:31]2[C:30]3[C:29]([C:43]([NH2:45])=[O:44])=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:36]=2[CH:35]=[C:34]([O:37][CH3:38])[CH:33]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 101569139-Benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamideHCID 68718528lithium aluminium hydride THF

Produkt 1

HCID 227398894-(2-Amino)ethyloxy-9-benzyl-2-methoxycarbazole-5-carboxamideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 1.25 ml (1.25 mmol) 1M lithium aluminum hydride/THF in 8.3 ml THF at 0° C. was added H2SO4(34.5 μl, 0.63 mmol) dropwise over 5 min. The mixture was allowed to stir at room temperature 1 hour, then a suspension of 9-benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamide (0.32 g, 0.83 mmol) in 8.3 ml THF was added dropwise at a rate which kept the temperature below 26° C. After an additional 45 minutes, the reaction was quenched with 0.32 ml 1:1 THF/H2O, 0.48 ml 13% NaOH, and finally 51 μl H2O. The reaction was diluted with EtOAc and saturated NaHCO3, and the layers separated. The organic layer was extracted with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH to give the subtitled product (148 mg, 46%). MS (ES+) 390

Aufarbeitung

  1. additionwas added dropwise at a rate which
  2. customthe temperature below 26° C
  3. waitAfter an additional 45 minutes
  4. customthe reaction was quenched with 0.32 ml 1:1 THF/H2O, 0.48 ml 13% NaOH, and finally 51 μl H2O
  5. additionThe reaction was diluted with EtOAc and saturated NaHCO3
  6. customthe layers separated
  7. extractionThe organic layer was extracted with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo
  10. customThe residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH

Quellen und Nachweise

ORD-Eintrag
ord-fa967103d34b4338a056995235c4af0d
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713645B1

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