Cesium carbonate → HCID 59374057, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial was added cesium carbonate (834 mg, 2.56 mmol), 4-(pyridin-2-ylamino)phenol (191 mg, 1.024 mmol), and 3-(2-fluoropyridin-3-yl)-1-methylcyclopentanol (200 mg, 1.024 mmol) followed by NMP (2049 μL). The slurry was heated to 200° C. for 3 h in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden). The reaction mixture was diluted with ethyl acetate (35 mL) and washed with 5N NaOH (5×30 mL) before drying over magnesium sulfate, filtering, and concentrating to a dark orange oil under reduced pressure. The oil was dissolved in 2 mL DMSO and transferred to a preparative HPLC vial through a 0.45 μm syringe filter. The crude compound was purified in three aliquots over 25 minutes per sample (5% 0.1% TFA in ACN:0.1% TFA in water to 80% over 15 minutes with a ten minute hold at 80%) on a Shimadzu Prominence Prep HPLC. The major peaks were collected and diluted with DCM (40 mL) before washed with saturated aqueous sodium bicarbonate (3×40 mL), drying over magnesium sulfate, filtering, and concentrating under reduced pressure, yielding the product as a yellow oil. MS (ESI, pos. ion) m/z: 362.3 (M+1). IC50 (uM) 0.035.

Provenance & Evidence