tert-Butanol → 4-(Biphenyl-2-ylamino)-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

Into a vial was added 4-bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (100 mg, 0.3 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (2.0 μl mg, 0.036 mmol), tris(dibenzylideneacetone)dipalladium(0) (11 mg, 0.012 mmol), [1,1′-Biphenyl]-2-amine (50.2 mg, 0.296 mmol), sodium tert-butoxide (86 mg, 0.89 mmol) and anhydrous tert-butyl alcohol (4.1 mL, 43 mmol). The reaction mixture was sparged with argon for ˜5 min. The septum was replaced with a microwave vial cap, and the reaction mixture was heated for 5 min at 120° C. The reaction mixture was then filtered through a syringe filter and the filtrate concentrated in vacuo. The vial and syringe were washed with 3 mL of DMSO and this was combined with the concentrated filtrate. The resulting solution was filtered through a plug of cotton then purified by reverse phase HPLC (Prep: Phenomenex 250×30.0 mm 15 micron C18 column. 40 mL/min. Gradient 15% B to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA). The clean fractions were concentrated in vacuo to afford the product as an off-white solid. LC/MS analysis: Retention time: 1.52 minutes, M+H=426.

Provenance & Evidence