Sodium Hydroxide → 1-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole

HRID 612846

Reaktionsgleichung

Reaktionsgleichung von HRID 612846
Br.[CH:2]1([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=3)[C:10]([CH2:18][CH3:19])=[N:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:2]1([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=3)[C:10]([CH2:18][CH3:19])=[N:9]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 195967561-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole hydrobromide

Produkt 1

HCID 98596991-Cyclohexyl-3-ethyl-6-fluoro-1H-indazoleAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 1-cyclohexyl-3-ethyl-6-fluoro-1H-indazole hydrobromide (0.440 g, 1.34 mmol) was added 1N aqueous sodium hydroxide (10 mL) and toluene (10 mL). The biphasic mixture was stirred for one hour and the layers were separated. The aqueous layer was reextracted with toluene (10 mL), and the organic extracts were combined, dried over magnesium sulfate, and concentrated to 1-cyclohexyl-3-ethyl-6-fluoro-1H-indazole (0.310 g, 94% yield). 1H NMR (400 MHz, CDCl3) δ 1.33 (t, 3, J=7.7), 1.35-1.44 (m, 2), 1.47-1.96 (m, 8), 2.93 (q, 2, J=7.7), 4.14-4.22 (m, 1), 6.81 (dt, 1, J=8.9, 2.1), 6.99 (dd, 1, J=9.8, 2.1), 7.40 (ddd, 1, J=8.7, 5.2, 0.4). 13C NMR (100 MHz, CDCl3) δ 13.97, 20.53, 25.37, 25.84, 32.32, 58.18, 94.77, (d, J=27.4), 109.11 (d, J=26.0), 119.38, 121.75 (d, J=11.5), 139.89 (d, J=13.0), 146.61, 161.95 (d, J=242).

Aufarbeitung

  1. customthe layers were separated
  2. dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-f388348b64c540dc98e86d29911b918e
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005118

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