Sodium Carbonate → HCID 57531208, compound

Participants

Reaction Conditions

Reaction Steps

Mix 9-bromomethylene-3,6-difluoro-9H-thioxanthene (104 mg, 0.32 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)- 1,3-dihydro-benzoimidazol-2-one (76 mg, 0.29 mmol), and Na2CO3 (2M/water, 363 μL, 0.73 mmol) in dioxane (2 mL) and sparge with nitrogen for 5 min. Add Pd(PPh3)4 (17 mg, 0.015 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 (50-60% THF/hexanes), then re-purify by semi-prep reverse-phase HPLC (10-95% CH3CN/H2O, 0.1% TFA added) to afford 19 mg (17%) of the title compound as a yellow foam. MS [ES] 379 (M+H), 377 (M−H); HPLC shows 100% purity;, 1H-NMR (DMSO-d6) δ 10.67 (s, 1H), 10.54 (s, 1H), 7.89 (dd, 1H, J=8.6, 5.5 Hz), 7.53 (dd, 1H, J=9.0, 2.9 Hz), 7.47 (dd, 1H, J=8.8, 2.6 Hz), 7.27 (m, 2H), 7.02 (m, 2H), 6.86 (dd, 2H, J=11.5, 8.4 Hz), 6.78 (s, 1H).

Provenance & Evidence