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

HRID 57567Notes

Reaction equation

HRID 57567 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.C(Cl)Cl>[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

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 16217653N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

Product 1

HCID 58354653N-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (0.5 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 atmosphere of nitrogen, then diluted with CH2Cl2 (20 mL), filtered through a plug of diatomaceous earth, rinsed with CH2Cl2 and evaporated to give product as a off-white solid. MS (m/z): 312 (M+H)+.

Workup

  1. filtrationfiltered through a plug of diatomaceous earth
  2. washrinsed with CH2Cl2
  3. customevaporated
  4. customto give product as a off-white solid

Sources & evidence

ORD record
ord-e83826c319dc40b08ef2c9fb2ca13813
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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