Bromine → Ethyl 5-bromo-2-(4-methyl-1-piperazinyl)-4-pyridinecarboxylate

HRID 1975954Notes

Reaction equation

HRID 1975954 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[CH:8]=1)[CH3:4].C(=O)(O)[O-].[Na+]>ClCCl.O>[CH2:3]([O:5][C:6](=[O:20])[C:7]1[C:12]([Br:1])=[CH:11][N:10]=[C:9]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[CH:8]=1)[CH3:4]

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 2762483Ethyl 2-(4-methylpiperazin-1-yl)pyridine-4-carboxylate

Product 1

HCID 11221145Ethyl 5-bromo-2-(4-methyl-1-piperazinyl)-4-pyridinecarboxylateYield 37.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.91 ml (17.7 mmol) Br2 was added dropwise to a solution of 2.95 g (11.8 mmol) 2-(4-methyl-piperazin-1-yl)-isonicotinic acid ethyl ester in 20 ml dichloromethane at 0° C.-4° C. Stirring was continued at room temperature for 1 h and 50 ml saturated sodium bicarbonate solution in water was added. The aqueous layer was separated and washed twice with dichloromethane. The combined organic layers were dried (magnesium sulfate) and evaporated. The residue was purified by chromatography to give 1.45 g (37%) of the title compound as a pale yellow oil.

Workup

  1. customThe aqueous layer was separated
  2. washwashed twice with dichloromethane
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. customevaporated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-51a2f18772b347b69b9a0b86eefab0f4
Source dataset
uspto-grants-2001_05
Patent number
US06225316B1

Reaction notes

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