反应详情

温度

100 °C

A solution of 1-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (422 mg, 1.32 mmol) and 2-chloro-4-iodo-furo[2,3-c]pyridin-7-ylamine (354 mg, 1.20 mmol) in 1,4-dioxane (8.06 mL) and H2O (2 mL) was charged with potassium carbonate (250 mg, 0.0018 mol) and (1,1′-bis(diphenylphosphino)ferrocene)palladium dichloride (9 mg, 0.01 mmol) under an atmosphere of nitrogen. The mixture was heated in a microwave at 100° C. for 40 min. The reaction mixture was dissolved in EtOAc and then washed with brine (2×). The aqueous layer was back-extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to a solid. The product was then purified by flash chromatography (0 to 5% 7 N NH3/MeOH:EtOAc) to afford 374 mg (86%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.05 (s, 1 H), 7.89 (s, 1 H), 7.83 (s, 1 H), 7.05 (s, 1 H), 4.67 (dd, J=13.52, 1.89 Hz, 1 H), 4.50 (tt, J=11.46, 4.20 Hz, 1 H), 4.08 (d, J=13.89 Hz, 1 H), 3.32-3.37 (m, 1 H), 2.79-2.91 (m, 1 H), 1.91-2.24 (m, 7 H). MS (ESI): 362.11 [M+H]+; HPLC tR=0.88 min (TOF: polar—3 min).

1. washwashed with brine (2×)
2. extractionThe aqueous layer was back-extracted with EtOAc (3×)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo to a solid
6. customThe product was then purified by flash chromatography (0 to 5% 7 N NH3/MeOH:EtOAc)