Sodium Carbonate → N-(3-Xanthen-9-ylidenemethyl-phenyl)-methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

Mix 9-Bromomethylene-9H-xanthene (400 mg, 1.46 mmol), N-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanesulfonamide (413 mg, 1.39 mmol), and Na2CO3 (2M/water, 1.74 mL, 3.48 mmol) in dioxane (10 mL) and sparge with nitrogen for 10 min. Add Pd(PPh3)4 (81 mg, 0.070 mmol), seal vial, and heat to 95° C. overnight. Concentrate and dilute with water (3 mL) and ethyl acetate (10 mL). Load mixture onto a Varian ChemElut CE1005 solid-phase extraction cartridge. Elute, collect, and concentrate 50 mL ethyl acetate. Purify on silica gel (20-40% ethyl acetate/hexanes), then re-purify by semi-prep reverse-phase HPLC (10-95% CH3CN/H2O, 0.1% TFA added) to afford 14 mg (3%) of the title compound as a yellow solid. MS [ES] 364 (M+H), 362 (M−H); HPLC shows 97% purity; 1H-NMR (CDCl3) δ 7.78 (d, 1H, J=7.5 Hz), 7.39-7.14 (m, 10H), 6.91 (s, 1H), 6.85 (t, 1H, J=7.5 Hz), 6.53 (s, 1H), 3.01 (s, 3H).

Provenance & Evidence