Reaction #710548

Reaction equation

4-bromo-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide

4-(methanesulfonyl)benzene boronic acid

Na2CO3

→

title compound

Yield 78.0%

4′-Methanesulfonyl-biphenyl-4-sulfonic acid isobutyl-(2-trifluoromethyl-phenyl)-amide

Yield 78.0%

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   OtherThe mixture was degassed
2. 2
   Otherpurged with nitrogen
3. 3
   Othermicrowave irradiation
4. 4
   workup.ADDITIONThe mixture was diluted with EtOAc
5. 5
   Washwashed with water (2×) and brine
6. 6
   Dryingdried over Na2SO4
7. 7
   Concentrationconcentrated under vacuum
8. 8
   OtherPurified by silica gel column chromatography (0-100% EtOAc in cyclohexane)
9. 9
   Othertriturating with diethyl ether

Procedure

A 2-5 mL microwave vial was charged with 4-bromo-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (108 mg, 0.248 mmol), 4-(methanesulfonyl)benzene boronic acid (60 mg, 0.298 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (18 mg, 0.025 mmol), 1M Na2CO3 solution (496 μL, 0.496 mmol) and 1,4-dioxane (2.5 mL). The mixture was degassed, purged with nitrogen and heated at 150° C. for 30 minutes using microwave irradiation. The mixture was diluted with EtOAc, washed with water (2×) and brine dried over Na2SO4 and concentrated under vacuum. Purified by silica gel column chromatography (0-100% EtOAc in cyclohexane) and triturating with diethyl ether gave the title compound (99 mg, 78% yield) as a white solid. 1H NMR (400 MHz, DMSO) δ 8.06-8.03 (m, 6H), 7.85 (dd, J=7.4, 2.1 Hz, 1H), 7.80-7.74 (m, 2H), 7.69-7.60 (m, 2H), 7.07 (d, J=7.7 Hz, 1H), 3.47 (dd, J=13.4, 8.7 Hz, 1H), 3.29 (s, 3H), 3.21 (dd, J=13.4, 4.8 Hz, 1H), 1.56-1.45 (m, 1H), 0.91 (d, J=6.5 Hz, 3H), 0.74 (d, J=6.7 Hz, 3H), LCMS (m/z Method B) ES+ 512.0 [M+1]+.

Source