Water → Ammonia

HRID 343401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343401
[H-].[Na+].[C:3]([O:7][C:8](=[O:26])[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([Br:25])=[CH:22][CH:23]=3)[NH:18][N:17]=2)[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1.O>CN(C=O)C>[NH3:10].[C:3]([O:7][C:8](=[O:26])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([Br:25])=[CH:22][CH:23]=3)[N:18]([CH2:32][C:31]3[CH:34]=[CH:35][C:28]([F:27])=[CH:29][CH:30]=3)[N:17]=2)[CH2:14][CH2:15]1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 178451205HCID 178451205, Verbindung

Produkt 2

HCID 222AmmoniaHCID 54441703{4-[6-Bromo-1-(4-fluoro-benzyl)-1H-indazol-3-yl]-piperidin-1-yl}-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (42 mg of a 60% dispersion in oil, 1.05 mmol) was added to a stirred solution of [4-(6-bromo-1H-indazol-3-yl)-piperidin-1-yl]-acetic acid tert-butyl ester (332 mg, 0.84 mmol) in DMF (7 ml) and after 30 min, a solution of 4-fluorobenzyl bromide (0.105 ml, 0.84 mmol), in DMF (7 ml) was added. The mixture stirred at +23° under nitrogen for 16 h, treated with water (25 ml), extracted with ethyl acetate (3×50 ml) and the combined, dried (Na2SO4) organic extracts were evaporated in vacuo to give an oil. This oil was purified by flash chromatography over silica gel (Merck 9385) eluting with dichloromethane--ethanol--880 ammonia (967:30:3) to give impure title compound. This was further purified by flash chromatography over silica gel (Merck 9385) eluting with ethyl acetate--cyclohexane (1:2) to give the title compound as a colourless oil (290 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. dry with materialdried (Na2SO4) organic extracts
  3. customwere evaporated in vacuo
  4. customto give an oil
  5. customThis oil was purified by flash chromatography over silica gel (Merck 9385)
  6. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-095fa4bcef114249aae3b31cd812c4d0
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861414

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