Hydrogen Bromide → 1-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole hydrobromide

HRID 612845

Reaction equation

HRID 612845 reaction equation
[CH:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=3)[C:9]([CH2:17][CH3:18])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BrH:19]>C1(C)C=CC=CC=1.C(O)(=O)C>[BrH:19].[CH:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=3)[C:9]([CH2:17][CH3:18])=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 98596991-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole

Product 1

HCID 195967561-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole hydrobromideYield 55%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

1-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole (2.00 g, 8.12 mmol) was dissolved in toluene (20 mL) and to the solution was added hydrobromic acid (1.62 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 1-cyclohexyl-3-ethyl-6-fluoro-1H-indazole hydrobromide (1.46 g, 55% yield) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 1.22 (t, 3, J=7.7), 1.38-1.45 (m, 2), 1.60-1.83 (m, 8), 2.83 (q, 2, J=7.7), 4.36-4.43 (m, 1), 6.85-6.90 (m, 1), 7.47 (dd, 1, J=10.3, 1.7), 7.68 (dd, 1, J=8.8, 5.3). 13C NMR (100 MHz, DMSO-d6) δ 13.98, 20.26, 25.44, 25.49, 32.52, 56.80, 95.64 (d, J=27.5), 109.32 (d, J=26.0), 119.23, 122.38 (d, J=11.5), 140.02 (d, J=13.0), 146.11, 161.795 (d, J=241).

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-fed40ac23c3946a6a8c006aa62457446
Source dataset
uspto-grants-1999_12
Patent number
US06005118

Linked notes

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