Benzyl Bromide → Methyl 3-bromo-6-(dibenzylamino)pyridine-2-carboxylate

HRID 887755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887755
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:11][C:12]1[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[C:15]([Br:22])=[CH:14][CH:13]=1>CN(C)C=O.C(OCC)C>[Br:22][C:15]1[C:16]([C:18]([O:20][CH3:21])=[O:19])=[N:17][C:12]([N:11]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10657127Methyl 6-amino-3-bromopyridine-2-carboxylate

Produkt 1

HCID 59145917Methyl 3-bromo-6-(dibenzylamino)pyridine-2-carboxylateAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 60% sodium hydride (880 mg, 22.0 mmol) and benzyl bromide (6.24 mL, 52.5 mmol) in N,N-dimethylformamide (80 mL) was added a solution of methyl 6-amino-3-bromopyridine-2-carboxylate (2.42 g, 10.5 mmol) in N,N-dimethylformamide (25 mL) under ice-cooling and the mixture was stirred for 30 min. The reaction solution was diluted with diethyl ether, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→20/80) to give the title compound (3.16 g, yield 73%).

Aufarbeitung

  1. temperaturecooling
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→20/80)

Quellen und Nachweise

ORD-Eintrag
ord-3ce9316cba1a4fb886aa8db671b1ff2d
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247429B2

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