tert-Butyl bromoacetate → HCID 178451205, Verbindung

HRID 343400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343400
Cl.[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:8][NH:9]2)=[CH:5][CH:4]=1.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH3:8].[C:23]([O:22][C:20](=[O:21])[CH2:19][N:15]1[CH2:16][CH2:17][CH:12]([C:7]2[C:6]3[C:10](=[CH:11][C:3]([Br:2])=[CH:4][CH:5]=3)[NH:9][N:8]=2)[CH2:13][CH2:14]1)([CH3:26])([CH3:25])[CH3:24]

Komponenten

6

Edukt 3

HCID 79177tert-Butyl bromoacetateHCID 516892Sodium BicarbonateHCID 178419305HCID 178419305, Verbindung

Produkt 2

HCID 222AmmoniaHCID 178451205HCID 178451205, VerbindungAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-3-piperidin-4-yl-1H-indazole hydrochloride (500 mg, 1.78 mmol), tert-butyl bromoacetate (0.29 ml, 1.78 mmol), sodium bicarbonate (150 mg, 1.87 mmol), and DMF (10 ml) was stirred at +23° under nitrogen for 18 h The mixture was evaporated in vacuo, treated with aqueous saturated sodium bicarbonate (25 ml), and extracted with ethyl acetate (50 ml). The dried (Na2SO4) organic layer was evaporated in vacuo onto silica gel (Merck 7734). Purification by flash chromatography over silica gel (Merck 9385), eluting with dichloromethane--ethanol--880 ammonia (gradient 967:30:3 to 945:50:5) afforded the title compound as fine white crystals (347 mg).

Aufarbeitung

  1. customwas evaporated in vacuo
  2. additiontreated with aqueous saturated sodium bicarbonate (25 ml)
  3. extractionextracted with ethyl acetate (50 ml)
  4. dry with materialThe dried (Na2SO4) organic layer
  5. customwas evaporated in vacuo onto silica gel (Merck 7734)
  6. customPurification by flash chromatography over silica gel (Merck 9385)
  7. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c3aeedb40bc8494e84ca2351578a8e66
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861414

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