Methyl iodide → 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:5][N:4]=1.[CH3:18]I>>[CH3:18][N:4]1[CH:5]=[C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:7]=[CH:8][C:3]1=[O:2]Participants
3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (235 mg, 1.00 mmol) and CH3I (426 mg, 3.00 mmol) was heated at 80° C. for 3 hours. The mixture was partitioned between ethyl acetate and H2O. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over MgSO4, and evaporated to dryness to afford 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one that was directly used in next step without further purification.
Workup
- customThe mixture was partitioned between ethyl acetate and H2O
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-fb7b7c2a888c4fd8b138678c4d0c53fc
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969386B2
Reaction notes
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