Potassium Fluoride → HCID 25014404, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-Chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)-N-methyl-N-phenylmethanesulfonamide (4.4 g, 10.36 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H pyrazole (2.59 g, 12.43 mmol), potassium fluoride (1.985 g, 34.2 mmol), tri-t-butylphosphonium tetrafluoroborate (0.270 g, 0.932 mmol), and Pd2(dba)3 (0.379 g, 0.414 mmol) were combined as solids and placed under a nitrogen atmosphere. DMF (104 ml) was added, the mixture was degassed, and then the reaction was heated to 130° C. with stirring for 2 h. After cooling to room temperature, the mixture was poured into aqueous sodium hydrogen carbonate (saturated, 250 mL) and extracted with dichloromethane (4×250 mL). The organic extracts were combined, dried over Na2 SO4, and concentrated under reduced pressure. The residue was then dissolved in hot dioxane (500 mL). Hexanes were added until a precipitate formed. After standing at room temperature overnight, the precipitate was collected to afford the title compound as a gray solid. 1H NMR (600 MHz, DMSO-D6) δ 9.22 (d, 1H); 8.53 (d, 1H); 8.47 (s, 1H); 8.15 (s, 1H); 8.14 (d, 1H); 7.78 (m, 2H); 7.39 (d, 1H); 7.32 (m, 5H); 7.20 (m, 1H); 4.75 (s, 2H); 3.88 (s, 3H); 3.23 (s, 3H). LRMS (APCI) calculated for C21H21N4O3S [M+H]+, 409.1; found 409.1.

Provenance & Evidence