Acetone → N-Methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

HRID 1262032Notes

Reaction equation

HRID 1262032 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:20]=[C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=2)[O:13]1.CI>ClCCl>[CH3:1][N:25]([C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([B:14]2[O:13][C:12]([CH3:30])([CH3:11])[C:16]([CH3:17])([CH3:18])[O:15]2)[CH:20]=1)[S:26]([CH3:29])(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 162177153-(Methanesulfonylamino)phenylboronic acid pinacol ester

Product 1

HCID 57416160N-Methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with Potassium carbonate (1.1 g, 8.1 mmol) and Acetone (40 mL, 500 mmol). To the suspension was added N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide (2.0 g, 6.7 mmol) followed by Methyl iodide (0.50 mL, 8.1 mmol). The mixture was stirred at room temperature for 18 hours. The reaction was then 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. The resulting white solid (2.00 g) was consistent for desired N-Methyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide and was used without further purification. 1H NMR (400 MHz, DMSO, d6) δ 7.63 (m, 1H), 7.60 (m, 1H), 7.49 (m, 1H), 3.24 (s, 3H), 2.97 (s, 3H), 1.30 (s, 12H).

Workup

  1. filtrationfiltered through a plug of diatomaceous earth
  2. washrinsed with dichloromethane
  3. customevaporated to a viscous oil
  4. waitThe material was subjected to high vacuum for 18 hours
  5. customwas used without further purification

Sources & evidence

ORD record
ord-65dbab01688e4552986bf70cf330fc43
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…