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

HRID 639324Notes

Reaction equation

HRID 639324 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]N1C(=O)CCC1=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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 45790075Methyl 5-(piperidin-1-yl)pyrazine-2-carboxylate

Product 1

HCID 866195226-Bromo-5-piperidin-1-yl-pyrazine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2 g (9 mmol) 5-piperidin-1-yl-pyrazine-2-carboxylic acid methyl ester and 1.69 g (9.4 mmol) N-bromosuccinimid in 30 mL CHCl3 was heated to 60° C. for 16 h. The mixture was concentrated and purified by flash column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to yield after evaporation of the product fractions 1.43 g (53%) of the title compound as white solid. m/z (ES+): 300.2 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash column chromatography on silica eluting with a gradient
  3. customformed from ethyl acetate and heptane
  4. customto yield
  5. customafter evaporation of the product fractions 1.43 g (53%) of the title compound as white solid

Sources & evidence

ORD record
ord-03c693fa11f2492cb19c754fc486d115
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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