Potassium Carbonate → HCID 59332804, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-6-fluoro-5,6-dihydro-1H-indole-7-carboxamide (9.2 mg, 0.024 mmol), phenylboronic acid (5.73 mg, 0.047 mmol), and K2CO3 (9.75 mg, 0.071 mmol) was taken up in 1,4-dioxane (0.3 mL) and water (0.150 mL). The mixture was degassed with argon for 10 min, and PdCl2(dppf) (1.721 mg, 2.351 μmol) was added. The vial was sealed, and the reaction was heated in a Biotage microwave for 5 min at 100° C. on high absorption. The aqueous layer was removed via pipette, and the reaction mixture was filtered through a Stratosphere PL-Thio MP SPE cartridge (0.5 g), eluting with 1:1 DCM/MeOH (10 mL). The eluent was concentrated under a stream of nitrogen at 50° C., and the crude product was dissolved in DMSO (1.2 mL) and purified on a Gilson HPLC (XBridge C18 5 μm OBD 19×100 mm preparatory column), eluting at 15 mL/min with a linear gradient running from 20% CH3CN/H2O (0.1% NH4OH) to 70% CH3CN/H2O (0.1% NH4OH) over 18 min. The desired fractions were concentrated under a stream of nitrogen at 50° C. and dried under high vacuum, giving 3.9 mg (43%) of the title compound.

Provenance & Evidence