Reaction #2006412

Reaction equation

28

4-(Benzenesulfonylamino)-phenyl Iodide

tri-o-tolylphosphine

Et3N

acrylic acid

→

title compound 35

Yield 99.0%

3-[4-(Benzenesulfonylamino)-phenyl]-2-propenoic Acid

Yield 99.0%

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe resulting solution was degassed
2. 2
   Otherpurged several times with N2
3. 3
   FiltrationThe solution was filtrated through a Celite pad with a fritted glass funnel
4. 4
   Otherthe filtrate was evaporated
5. 5
   OtherThe residue was purified by flash chromatography

Procedure

To a solution of 28 (500 mg, 1.39 mmol), in DMF (10 mL) at room temperature were added tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; 38 mg, 1.67 mmol), tri-o-tolylphosphine (P(o-tol)3, 25 mg, 0.83 mmol), Et3N (483 μL, 3.48 mmol) and finally acrylic acid (84 μL, 1.67 mmol). The resulting solution was degassed and purged several times with N2 then heated overnight at 100° C. The solution was filtrated through a Celite pad with a fritted glass funnel then the filtrate was evaporated. The residue was purified by flash chromatography using CH2Cl2/MeOH (95:5) as solvent mixture yielding the title compound 35 (415 mg, 99%) as yellowish solid.

Source