Potassium Carbonate → HCID 90341022, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide (110 mg, 0.22 mmol), 2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (50 mg, 0.18 mmol) and K2CO3 (50 mg, 0.366 mmol) in 1,4-dioxane (2 mL) were added X-Phos (10 mg) and Pd2(dba)3 (10 mg) under N2. The reaction mixture was stirred at 100° C. for 5 hours and concentrated in vacuo to remove 1,4-dioxane. The reaction mixture was extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and evaporated concentrated in vacuo. The residue was purified by prep-HPLC to give the desired product (50 mg, yield: 44%). 1H-NMR (CDCl3, 400 MHz) δ 8.67 (s, 1H), 8.51 (s, 1H), 7.70˜7.73 (m, 3H), 7.52 (d, J=8.0 Hz, 1H), 7.27 (s, 1H), 7.23 (s, 1H), 7.14˜7.20 (m, 3H), 6.80 (t, J=8.0 Hz, 1H), 5.56 (br s, 1H), 4.36 (t, J=6.4 Hz, 2H), 3.51 (s, 3H), 3.34 (t, J=6.4 Hz, 2H), 2.85 (d, J=4.8 Hz, 3H), 2.63 (s, 3H). MS (M+H)+: 613.

Provenance & Evidence