Reaction #333

Reaction equation

Clc1ccnc(Cl)n1

Nc1cccc(S(N)(=O)=O)c

→

NS(=O)(=O)c1cccc(Nc2

Yield 2.0%

Solvents

C1COCCO1

Conditions

Procedure

2,4-dichloropyrimidine (200 mg, 1.34 mmol), 3-aminobenzenesulfonamide (231 mg, 1.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (93 mg, 0.16 mmol), cesium carbonate (875 mg, 2.68 mmol) and diacetoxypalladium (15.07 mg, 0.07 mmol) were suspended in dioxane (5 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (150 mL) and washed with water (150 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 4% (10:1 MeOH/NH3 (aq)) in DCM. NMR analysis showed a trace amount of product.

Source