Hydrogen Bromide → 6-bromo-1-cyclohexyl-3-ethyl-1H-indazole hydrobromide

HRID 849319Notes

Reaction equation

HRID 849319 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:17][CH3:18])=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1.Br>C1(C)C=CC=CC=1.C(O)(=O)C>[BrH:1].[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:17][CH3:18])=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 118089646-Bromo-1-cyclohexyl-3-ethyl-1H-indazole

Product 1

HCID 195914236-bromo-1-cyclohexyl-3-ethyl-1H-indazole hydrobromideYield 251.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

6-Bromo-1-cyclohexyl-3-ethyl-1H-indazole (1.015 g, 3.304 mmol) was dissolved in toluene (10 mL) and to the solution was added hydrobromic acid (1.5 mL of a 30% solution in acetic acid). The solution was stirred at room temperature 30 minutes and concentrated to low volume. Ethyl acetate (10 mL) was added, the solids were filtered and washed with additional ethyl acetate (10 mL) to provide 6-bromo-1 cyclohexyl-3-ethyl-1H-indazole hydrobromide (1.612 g, 80%) as a white solid (mp 170-172° C. (decomposition)). 1H NMR (400 MHz, DMSO) δ 1.24 (t, 3, J=7.5), 1.42-1.45 (m, 2), 1.64 (d, 1, J=12.9), 1.76-1.87 (m, 7), 2.85 (q, 2, J=7.5), 4.46-4.52 (m, 1), 7.14 (dd, 1, J=8.5, 1.5), 7.63 (dd, 1, J=8.5, 0.8), 7.93 (d, 1, J=1.0), 9.93 (bs, 1). 13C NMR (100 MHz, DMSO) δ 13.99, 20.23, 25.47, 32.70, 56.67, 112.69, 119.90, 121.06, 122.42, 122.98, 140.57, 146.18.

Workup

  1. concentrationconcentrated to low volume
  2. additionEthyl acetate (10 mL) was added
  3. filtrationthe solids were filtered
  4. washwashed with additional ethyl acetate (10 mL)

Sources & evidence

ORD record
ord-5a6fe435250a40e1a6c74914b242cb98
Source dataset
uspto-grants-2000_01
Patent number
US06011159

Reaction notes

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