N-bromobutanimide → HCID 54388605, compound

HRID 1254075Notes

Reaction equation

HRID 1254075 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[N:10][CH:11]=1)=[CH2:5])C.C1C(=O)N([Br:23])C(=O)C1>C1COCC1.O>[Br:23][CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[N:10][CH:11]=1)=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58119338HCID 58119338, compound

Product 1

HCID 54388605HCID 54388605, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of step 1 product (780 mg, 3.76 mmol) in THF (37.5 ml) and H2O (2.5 ml) was added NBS (670 mg, 3.76 mmol) in one portion. The solution was stirred at rt for 10 min, solvent was removed and purified on silica gel column eluting a gradient of 8-75% EtOAc in hexane to afford methyl 5-(bromoacetyl)pyridine-2-carboxylate (0.92 g) LCMS: [M+H]+=258.1, 260.1.

Workup

  1. customsolvent was removed
  2. custompurified on silica gel column
  3. washeluting a gradient of 8-75% EtOAc in hexane

Sources & evidence

ORD record
ord-52db88a1596d4c6b937baff0dce742ca
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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