Methyl iodide → N-(6-methoxy-5-methylpyridin-2-yl)acetamide
Reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[N:6]=1)(=O)C.IC>CO.C(Cl)Cl>[CH3:1][O:4][C:5]1[N:6]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[CH:8]=[CH:9][C:10]=1[CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
To a stirred solution of 6-acetamido-3-methylpyridin-2-yl acetate (3.44 g, 16.5 mmol) in 2:1 MeOH/DCM (105 mL) at rt was added Ag2CO3 (9.11 g, 33.0 mmol) followed by iodomethane (3.09 mL, 49.6 mmol). The resulting mixture was stirred at 35° C. for 18 h then stood at rt for 2 d. The reaction mixture was combined with 2 previous batches derived from 6-acetamido-3-methylpyridin-2-yl acetate (590 mg, 2.83 mmol and 3.44 g, 16.5 mmol) and the combined batches were filtered through celite, rinsing with DCM. After concentration of the filtrate in vacuo purification by gradient column chromatography eluting with 20-50% EtOAc in heptane yielded the title compound (4.27 g, 23.7 mmol) as a white solid.
Workup
- waitthen stood at rt for 2 d
- filtrationthe combined batches were filtered through celite
- washrinsing with DCM
- customAfter concentration of the filtrate in vacuo purification by gradient column chromatography
- washeluting with 20-50% EtOAc in heptane
Sources & evidence
- ORD record
- ord-3b6825dd39994299baeddc5f38fe9686
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249160B2
Reaction notes
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