Sodium Carbonate → HCID 25123580, compound

Participants

Reaction Conditions

Reaction Steps

Into a 5 mL Personal Chemistry microwave reaction vial were added 4-Chloro-3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (38 mg, 0.075 mmol), 2-(5-Bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (29 mg, 0.12 mmol; preparation described below), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (3 mg, 0.004 mmol), acetonitrile (1 mL) and saturated aqueous Na2CO3 (75 μL). The vial was purged with nitrogen, sealed, and irradiated in a Personal Chemistry Optimizer at 120° C. for 30 min. Sodium sulfate was added to the reaction mixture and the slurry was filtered over Celite and concentrated. The crude product was dissolved in 1 mL TFA and stirred at 23° C. for 15 min. The solvent was evaporated and the resulting oil was dissolved in 1 mL DMSO and 50 μL ethylenediamine and purified by mass triggered reverse phase HPLC to afford the title compound (9.5 mg, 0.015 mmol, 25% yield). 1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.58 (m, 2H), 8.20 (s, 1H), 7.83 (t, J=2 Hz, 1H), 7.33 (td, J=8 Hz, J2=1.5 Hz, 1H), 7.27 (dd, J=7 Hz, J2=1.5 Hz, 1H), 7.05 (d, J=8 Hz, 1H), 6.95 (td, J=8 Hz, J2=1 Hz, 1H), 5.81 (d, J=6.5 Hz, 1H), 5.56 (d, J=6.5 Hz, 1H), 3.68 (s, 3H), 2.95 (s, 3H), 2.84 (s, 3H). MS: m/z 437.0 (M+H+).

Provenance & Evidence