Potassium Carbonate → HCID 25152788, compound

Participants

Reaction Steps

To a mixture of 4-({[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}methyl)cyclohex-1-en-1-yl trifluoromethanesulfonate (50 mg, 0.091 mmol, INTERMEDIATE 5) and 4-fluorophenyl boronic acid (25 mg, 0.179 mmol) in tetrahydrofuran (2 ml) and 1 M aqueous potassium carbonate (1 ml, 1.000 mmol) was added 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (1 mg, 5.64 μmol). The mixture was microwaved at 100° C. in a sealed tube for 10 min, cooled, and then resubmitted to the reaction conditions for 10 min, at which point LC/MS analysis showed no starting material. The organic phase of the reaction mixture was added directly to a 25 samplet and purified by flash chromatography on a Biotage Horizon, 25M column, eluting with 1 column volume of 100% dichloromethane followed by a gradient of 0 to 100% ethyl acetate in dichloromethane over 10 column volumes, to provide the title compound (37.5 mg, 0.076 mmol, 83% yield). Mass spectrum (ESI) 494.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.32 (d, J=8.5 Hz, 2H); 7.96 (d, J=8.0 Hz, 2H), 7.93 (d, J=1.5 Hz, 1H); 7.51 (s, 1H), 7.32 (ddd, J=2.0, 5.5, 8.5 Hz, 2H), 6.99 (t, J=9.0 Hz, 2H), 6.39 (br t, J=5.5 Hz, 1H), 6.03 (s, 1H), 3.42-3.58 (m, 3H), 2.34-2.56 (m, 3H), 1.96-2.08 (m, 3H), 1.46 (d, J=7.0 Hz, 6H), 1.44-1.62 (m, 2H).

Provenance & Evidence