Hydrogen Bromide → 1H-Pyrazole-5-carboxylic acid, 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-, ethyl ester

HRID 646640Notes

Reaction equation

HRID 646640 reaction equation
[BrH:1].Cl[C:3]1[CH2:7][CH:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[N:4]=1>BrCBr>[Br:1][C:3]1[CH2:7][CH:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[N:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 11701977HCID 11701977, compound2×

Product 1

HCID 100653831H-Pyrazole-5-carboxylic acid, 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-, ethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 3024DibromomethaneSolvent

Procedure

Hydrogen bromide was passed through a solution of ethyl 3-chloro-1-(3-chloro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxylate (i.e. product of Step B) (8.45 g, 29.3 mmol) in dibromomethane (85 mL). After 90 minutes the gas flow was terminated, and the reaction mixture was washed with aqueous sodium bicarbonate solution (100 mL). The organic phase was dried and evaporated under reduced pressure to give the title product as an oil (9.7 g, 99% yield), which crystallized on standing.

Workup

  1. customAfter 90 minutes the gas flow was terminated
  2. washthe reaction mixture was washed with aqueous sodium bicarbonate solution (100 mL)
  3. customThe organic phase was dried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-caa8470d5afa4ec3973e2a337cddd786
Source dataset
uspto-grants-2010_04
Patent number
US07705160B2

Reaction notes

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