Potassium Carbonate → 1-(4-{4-[7-amino-2-(6-fluoro-1H-indol-3-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)ethanone

Participants

Reaction Steps

To a nitrogen degassed solution of 1-{4-[4-(7-amino-2-chloro-furo[2,3-c]pyridin-4-yl)-pyrazol-1-yl]-piperidin-1-yl}ethanone (0.050 g, 0.14 mmol) in 4:1 1,4-dioxane:water (10 mL) was added 6-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (0.060 g, 0.143 mmol), potassium carbonate (0.047 g, 0.34 mmol), dichlorobis(triphenylphosphine)palladium (16 mg, 0.023 mmol). The mixture was heated at reflux for 3 h, then cooled to room temperature and concentrated. The residue was suspended in water and extracted with ethyl acetate (3×50 mL). The combined organic fractions were washed with water (15 mL), dried, and evaporated. Purification by flash chromatography (5% MeOH:DCM) afforded 18 mg (28%) of the title compound as a solid. 1H NMR (300 MHz, CDCl3): δ 1.99-2.14 (m, 2H), 2.17 (s, 3H), 2.24-2.34 (m, 2H), 2.81 (t, J=12 Hz, 1H), 3.29 (m, 1H), 4.02 (d, J=14.7 Hz, 1H), 4.40-4.48 (m, 1H), 4.78 (br. s, 2H), 4.78-4.82 (m, 1H), 6.97 (s, 1H), 7.07 (dt, J=9 Hz, 2.4 Hz, 1H), 7.16 (dd, J=9 Hz, 2.4 Hz, 1H), 7.70 (s, 1H), 7.78 (d, J=2.7 Hz, 1H), 7.87 (s, 1H), 7.92-7.97 (m, 2H), 8.94 (brs, 1H); MS (ESI): 459 [M+H]+.

Provenance & Evidence