Hydrogen Bromide → HCID 86657922, compound

HRID 2359040Notes

Reaction equation

HRID 2359040 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[N:10][N:11]([CH:13]([CH2:15][CH3:16])[CH3:14])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[BrH:23].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Br:23][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[N:10][N:11]([CH:13]([CH2:15][CH3:16])[CH3:14])[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 866579212-Chloro-4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine

Product 1

HCID 86657922HCID 86657922, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

To 2-Chloro-4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (0.57 mmol) was added slowly 0.5 mL of a 33% solution hydrobromic acid in acetic acid. The resulting mixture was stirred in the microwave at 140° C. for 20 min. After cooling to room temperature, potassium carbonate (2 molar solution) was added and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried over MgSO4 and evaporated. The residue was purified by chromatography on silica gel (hepthane:ethyl acetate 5:1 to 2:1) to afford 178 mg of 2-bromo-4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (79% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel (hepthane:ethyl acetate 5:1 to 2:1)

Sources & evidence

ORD record
ord-cd8451ea51e24a4db82165bd7a64a8f0
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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