Acetone → N-Methyl-N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide
Reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CC(C)=O.[CH3:11][C:12]1([CH3:30])[C:16]([CH3:18])([CH3:17])[O:15][B:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[O:13]1.IC>ClCCl>[CH3:1][N:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[B:14]1[O:13][C:12]([CH3:30])([CH3:11])[C:16]([CH3:17])([CH3:18])[O:15]1)[S:26]([CH3:29])(=[O:28])=[O:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A round bottom flask was charged with potassium carbonate (0.56 g, 4.0 mmol) and acetone (20 mL). To the suspension was added N-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide (1.0 g, 3.4 mmol) followed by iodomethane (0.25 mL, 4.0 mmol). The mixture was stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane (20 mL), filtered through a plug of diatomaceous earth, rinsed with dichloromethane and evaporated to a viscous oil. The material was subjected to high vacuum for 18 hours. N-Methyl-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide was isolated as a white solid (1.01 g, 95%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.81 (dd, J=7.5, 1.4 Hz, 1H), 7.47 (ddd, J=7.9, 7.9, 1.5 Hz, 1H), 7.38 (dd, J=7.9 Hz, 1H), 7.35-7.30 (m, 1H), 3.32 (s, 3H), 2.93 (s, 3H). MS=334 (M+Na)+.
Workup
- filtrationfiltered through a plug of diatomaceous earth
- washrinsed with dichloromethane
- customevaporated to a viscous oil
- waitThe material was subjected to high vacuum for 18 hours
Sources & evidence
- ORD record
- ord-2de7d1afcc264433a30805577aa6fe16
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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