[(4-Iodophenyl)sulfonyl]-2-pyridylamine → Methyl 2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

Participants

Reaction Conditions

Reaction Steps

4-Iodo-N-(2-pyridinyl)benzenesulfonamide (35 g, 97 mmol) was dissolved in a mixture of triethylamine and tetrahydrofuran (750+750 ml). The mixture was deaerated with nitrogen and dichlorobis(triphenylphosphine)palladium (1.2 g, 1.7 mmol) and copper(I) iodide (0.6 g, 3.4 mmol) were added. Finally methyl 5-ethynyl-2-hydroxybenzoate (23 g, 130 mmol) was added. The mixture was heated to 60° C. for 4 h, evaporated to dryness. The residue was dissolved in chloroform (1000 ml) and washed with water (3 x 200 ml) and dried with MgSO4. The solvent was evaporated in vacuo. Yield 31 g (77% ). The product can be purified by flash-chromatography on silica with chloroform as the eluent.

Provenance & Evidence