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tert-Butyldimethylsilyl chloride → 7-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amine

HRID 549188
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 549188
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C@@H:16]([CH3:19])[CH2:17][OH:18])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C@@H:16]([CH3:19])[CH2:17][O:18][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1
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Komponenten

5

Edukt 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 67157472(2S)-2-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol

Produkt 1

HCID 671576277-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 1049
Pyridine
Lösungsmittel

Versuchsvorschrift

A solution of (2S)-2-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol (30.0 g, 92.0 mmol) dissolved in 100 mL of anhydrous pyridine was treated with tert-butyldimethylsilyl chloride (15.2 g, 101.2 mmol) and a catalytic amount of DMAP (112 mg, 0.92 mmol). After stirring overnight at ambient temperature under an atmosphere of N2, the reaction mixture was concentrated under reduced pressure. The resulting solid was partitioned between CH2Cl2 (500 mL) and H2O (500 mL). The layers were separated and the organic portion was concentrated under reduced pressure to give 40.5 g of 7-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amine as a yellow, crystalline solid.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe resulting solid was partitioned between CH2Cl2 (500 mL) and H2O (500 mL)
  3. customThe layers were separated
  4. concentrationthe organic portion was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-23eb8d9eec764998a0400959cb8564f7
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07943609B2

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