Water → 3-Bromo-5-bromomethyl-2-methoxy-pyridine
Reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.O>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[C:6]([CH2:8][Br:18])[CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 3-bromo-2-methoxy-5-methyl-pyridine (Step AM3) (3.0 g, 14.7 mmol), was added NBS (3.1 g, 17.6 mmol) and AIBN (121 mg, 0.7 mmol) and the mixture was stirred at 80° C. for 1 h. H2O and CH2Cl2 were added and the phases were separated. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (heptane/EtOAc, 95:5→0:100). tR: 1.10 min (LC-MS 1).
Workup
- customthe phases were separated
- dry with materialThe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by silica gel column chromatography (heptane/EtOAc, 95:5→0:100)
Sources & evidence
- ORD record
- ord-7914d3c9fc9743d8900aa49bc7b48a04
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365576B2
Reaction notes
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