Reaction #710541

Reaction equation

Water

C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-methanesulfonamide

K2CO3

1-iodo-2-methylpropane

→

C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-N-isobutyl-methanesulfonamide

Yield 60.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Extractionthe reaction extracted with EtOAc
2. 2
   Washwashed with brine
3. 3
   Dryingdried with Na2SO4
4. 4
   Concentrationconcentrated
5. 5
   Otherpurified by silica gel column chromatography (0-50% DCM in cyclohexane)

Procedure

To a mixture of C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-methanesulfonamide (0.61 g, 1.68 mmol) and K2CO3 (464 mg, 3.4 mmol) in dimethylformamide (5 mL) was added 1-iodo-2-methylpropane (584 μL, 5.0 mmol). The mixture was heated at 100° C. in microwave reactor for 3 hours. Water was added and the reaction extracted with EtOAc, washed with brine, dried with Na2SO4, concentrated and purified by silica gel column chromatography (0-50% DCM in cyclohexane) to give C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-N-isobutyl-methanesulfonamide (423 mg, 1.0 mmol, 60%). LCMS (m/z, Method A) ES+ 415.8 [M+1]+.

Source