Sodium Hydroxide → 6-Bromo-1-cyclohexyl-3-ethyl-1H-indazole

HRID 849320Notes

Reaction equation

HRID 849320 reaction equation
Br.[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][CH3:19])=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][CH3:19])=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 195914236-bromo-1-cyclohexyl-3-ethyl-1H-indazole hydrobromide

Product 1

HCID 118089646-Bromo-1-cyclohexyl-3-ethyl-1H-indazoleYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 6-bromo-1-cyclohexyl-3-ethyl-1H-indazole hydrobromide (0.890 g, 2.30 mmol) was added 1N aqueous sodium hydroxide (20 mL) and toluene (20 mL). The biphasic mixture was stirred for one hour and the layers separated. The aqueous layer was reextracted with toluene (10 mL), and the organic extracts were combined, dried over magnesium sulfate, and concentrated to provide 6-bromo-1-cyclohexyl-3ethyl-1H-indazole (0.660 g, 94% yield). 1H NMR (400 MHz, CDCl3) δ 1.35 (t, 3, J=7.7), 1.39-2.06 (m, 10), 2.95 (q, 2, J=7.7), 4.21-4.28 (m, 1), 7.15 (d, 1, J=8.5), 7.51 (d, 1, J=8.5), 7.56 (s, 1). 13C NMR (100 MHz, CDCl3) δ 13.95, 20.50, 25.35, 25.84, 32.44, 58.15, 112.01, 120.10, 121.37, 121.65, 122.82, 140.37, 146.60. IR 2934, 2855, 1606, 1502, 1451, 1048, 951, 834 cm1. Analysis calculated for C15H19BrN2 : C, 58.64; H, 6.23; N, 9.12. Found: C, 58.82; H, 6.20; N, 9.01.

Workup

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

Sources & evidence

ORD record
ord-72090bc34c5b499c8b766be11c1939bd
Source dataset
uspto-grants-2000_01
Patent number
US06011159

Reaction notes

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