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

HRID 1523991Notes

Reaction equation

HRID 1523991 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][CH:12]=[CH:11][C:10]=2[NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[O:3]1.[C:21]([O-])([O-])=O.[K+].[K+].CC(C)=O.IC>C(OCC)(=O)C>[CH3:21][N:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[B:4]1[O:3][C:2]([CH3:20])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]1)[S:16]([CH3:19])(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 43565252-(Methanesulfonylamino)phenylboronic acid pinacol ester

Product 1

HCID 66980795N-Methyl-N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask under nitrogen were added N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (250 mg, 0.84 mmol), K2CO3 (140 mg, 1.01 mmol) and acetone (5.0 mL). Iodomethane (0.06 mL, 1 mmol) was then added to the mixture dropwise and the reaction stirred for 18 hours at rt. The reaction was then diluted with ethyl acetate (100 mL), washed with water (2×) and brine (1×), dried (Na2SO4) and concentrated to dryness. The crude product was purified by FCC providing the title compound (230 mg, 88%). 1H NMR (400 MHz, CDCl3) δ 7.82 (dd, J=7.3, 1.8, 1H), 7.51-7.43 (m, 1H), 7.40-7.29 (m, 2H), 3.32 (s, 3H), 2.93 (s, 3H), 1.36 (s, 12H).

Workup

  1. washwashed with water (2×) and brine (1×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to dryness
  4. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-12687f567b12449db022474812bbbf55
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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