Sodium Carbonate → HCID 86271203, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 61A (129 mg, 0.528 mmol), 2-(4,4-difluorocyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (129 mg, 0.528 mmol), and bis(triphenylphosphine)palladium(II) dichloride (28.5 mg, 0.041 mmol) in 10 mL dimethoxyethane/ethanol/water (7/2/3) was added sodium carbonate (129 mg, 1.219 mmol). The reaction was stirred at 100° C. for 2 hours, cooled and then extracted with ethyl acetate. The organic fraction was washed with saturated sodium bicarbonate, water and brine, then dried over magnesium sulfate and concentrated. The crude material was triturated with ethyl acetate, and the solid was collected by filtration. The solid was purified via flash chromatography: Analogix Intelliflash™ 280, 24 g silica column, 20% to 60% ethyl acetate/hexanes gradient over 30 minutes to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 12.27 (s, 1H) 8.65-8.90 (m, 1H) 7.09-7.48 (m, 3H) 6.45 (s, 1H) 6.37 (s, 1H) 3.73-3.82 (m, 3H) 2.80 (t, J=14.19 Hz, 2H) 2.69 (t, J=5.95 Hz, 2H) 2.08-2.27 (m, 2H). MS (ESI+) m/z 360.2 (M+H)+.

Provenance & Evidence