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

HRID 612846Notes

Reaction equation

HRID 612846 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-f388348b64c540dc98e86d29911b918e
Source dataset
uspto-grants-1999_12
Patent number
US06005118

Reaction notes

Loading…