Water → 6-Bromo-5-piperidin-1-yl-pyrazine-2-carboxylic acid methyl ester

HRID 639310Notes

Reaction equation

HRID 639310 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][N:6]=1)=[O:4].[Br:17]Br.C(Cl)Cl.O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7]([Br:17])[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24408BromineHCID 45790075Methyl 5-(piperidin-1-yl)pyrazine-2-carboxylate

Product 1

HCID 866195226-Bromo-5-piperidin-1-yl-pyrazine-2-carboxylic acid methyl esterYield 14.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.625 g (2.8 mmol) 5-piperidin-1-yl-pyrazine-2-carboxylic acid methyl ester, 1.12 g (7 mmol) Br2 and 0.142 g (0.48 mmol) FeBr3 in 10 mL CHCl3 was stirred at room temperature for 16 h. The mixture was treated with DCM and water and the organic layer separated and dried with MgSO4. 0.12 g (14%) of the title compound was obtained after evaporation as light yellow crystals which were used without further purification. m/z (ES+): 299.9 (M+H).

Workup

  1. customthe organic layer separated
  2. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-1bf538fc714a4526b1db7bd5a2b38088
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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