Methyl iodide → 3-Bromo-2-methoxy-4-methylpyridine

HRID 1753764Notes

Reaction equation

HRID 1753764 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:10]I>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 134638133-Bromo-4-methylpyridin-2-ol

Product 1

HCID 219528033-Bromo-2-methoxy-4-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-4-methyl-2-pyridone V-b (2.20 g, 11.7 mmol), in DCM (80 mL) was treated with MeI (7.29 mL, 117 mmol) and Ag2CO3 (6.47 g, 23.5 mmol). The flask was stoppered and stirred under argon for 6 days. The mixture was filtered and purified by column chromatography (SiO2, 10% EtOAc in cyclohexane) to afford the desired product V-c as a clear mobile oil (1.83 g, 80%). 1H NMR (300 MHz, CDCl3) δ 7.94 (d, J=5.0 Hz, 1H), 6.77 (d, J=5.1 Hz, 1H), 4.00 (s, 3H), 2.39 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. custompurified by column chromatography (SiO2, 10% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-8ba247b0b8f7402aaa59d58585a58bf7
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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