Potassium Carbonate → HCID 25123579, compound

Participants

Reaction Steps

Into a 5 mL Personal Chemistry microwave reaction vial were added 3-[4-Chloro-3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide (37 mg, 0.09 mmol), trimethylboroxine (15 μL, 0.11 mmol), tetrakis(triphenylphosphine)palladium (7 mg, 0.009 mmol), potassium carbonate (52 mg, 0.27 mmol), and dioxane (1 mL). The vial was purged with nitrogen, sealed, and irradiated in a Personal Chemistry Optimizer at 140° C. for 60 min. The reaction mixture was diluted with ethylacetate, filtered over Celite and concentrated. The crude product was purified by mass triggered reverse phase HPLC to afford the title compound (2.4 mg, 0.006 mmol, 7% yield). 1H NMR (500 MHz, DMSO-d6) δ 11.74 (d, J=2 Hz, 1H), 8.32 (s, 1H), 8.04 (s, 1H), 7.50 (t, J=8 Hz, 1H), 7.41 (dt, J1=9.5 Hz, J2=1.5 Hz, 1H), 7.37 (dt, J=7.5 Hz, J2=1.5 Hz, 1H), 7.33 (m, 4H), 7.26 (dd, J1=7 Hz, J2=2 Hz, 1H), 7.04 (d, J=7.5 Hz, 1H), 6.97 (td, J=7.5 Hz, J2=1 Hz, 1H), 3.70 (s, 3H), 2.97 (bs, 3H), 2.93 (bs, 3H), 2.04 (s, 3H). MS: m/z 386.2 (M+H+).

Provenance & Evidence