1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-(1-tert-butyl-3-(4-chlorobenzyl)-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-iodo-N-thiazol-2-yl-benzenesulfonamide (100 mg, 0.3 mmol, 1.0 equiv), tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol, 0.04 equiv), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (19 mg, 0.033 mmol, 0.12 equiv) and 2-tert-butyl-5-(4-chloro-benzyl)-2H-pyrazole-3-ylamine (86 mg, 0.33 mmol, 1.2 equiv) in 3.7 mL of anhydrous 1,4-dioxane was added sodium tert-butoxide (79 mg, 0.82 mmol, 3.0 equiv). The vial was capped, and the reaction mixture was heated 30 min at 150° C. in the microwave. The crude reaction mixture was filtered through celite then concentrated in vacuo. The residue was taken up in chloroform-methanol, concentrated onto celite, and purified via automated flash chromatography (12 g SiO2, gradient from hexanes to ethyl acetate). The appropriate fractions were collected, concentrated in vacuo, then lyophilized from water-acetonitrile to afford the product as an off-white solid (60 mg, 40%).

Provenance & Evidence