Methyl iodide → N-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide
Reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=2)[O:3]1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.ClCCl>[CH3:21][N:15]([C:12]1[CH:11]=[CH:10][C:9]([B:4]2[O:3][C:2]([CH3:20])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:14][CH:13]=1)[S:16]([CH3:19])(=[O:18])=[O:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide (0.50 g, 1.7 mmol) and potassium carbonate (0.28 g, 2.0 mmol) in acetone (10 mL) was added methyl iodide (0.12 mL, 2.0 mmol). The mixture was stirred at room temperature for 18 hours under an atmosphere of nitrogen then diluted with dichloromethane (20 mL), filtered through a plug of diatomaceous earth, rinsed with dichloromethane and evaporated. The material was subjected to high vacuum for 18 hours. N-Methyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide was isolated as a yellow solid (0.50 g, 95%) and was used without further purification. 1H NMR (400 MHz, CDCl3, δ, ppm): 7.83 (d, J=7.9 Hz, 2H), 7.39 (d, J=7.8 Hz, 2H), 3.34 (s, 3H), 2.82 (s, 3H), 1.34 (s, 12H). MS=312 (MH)+.
Workup
- filtrationfiltered through a plug of diatomaceous earth
- washrinsed with dichloromethane
- customevaporated
- waitThe material was subjected to high vacuum for 18 hours
Sources & evidence
- ORD record
- ord-28acc21252d54b86919488125e185593
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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