Potassium Carbonate → HCID 66760278, 화합물 (HRID 389589)｜HGS AIchem

실험 절차

A 2:1 mixture of 4-iodo-2-(1-methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)furo[2,3-c]pyridin-7-amine and 4-iodo-2-(2-methyl-2H-pyrazolo[3,4-c]pyridin-3-yl)furo[2,3-c]pyridin-7-amine (0.042 g, 0.102 mmol) and 1-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (0.041 g, 0.13 mmol) were dissolved in 1,4-dioxane (2 mL) and water (0.8 mL). The mixture was degassed with nitrogen for 10 min. To this mixture was added potassium carbonate (0.0530 g, 0.383 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride dichloromethane adduct (0.0104 g, 0.0128 mmol), and the mixture was heated to 80° C. for 5 h. Purification of the residue by MDP afforded 0.0143 g (29%) of 1-(4-{4-[7-amino-2-(1-methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)pethanone as a yellow gum (Ex. 363), and 0.0075 g (30%) 1-(4-{4-[7-amino-2-(2-methyl-2H-pyrazolo[3,4-c]pyridin-3-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)ethanone as a yellow gum (Ex. 364). 1-(4-{4-[7-amino-2-(1-methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)ethanone: 1H NMR (400 MHz, CD3OD): δ 9.77 (s, 1 H), 9.11 (d, J=5.8 Hz, 1 H), 8.60 (d, J=6.3 Hz, 1 H), 8.35 (s, 1 H), 8.03 (d, J=0.5 Hz, 1 H), 7.97 (s, 1 H), 7.89 (s, 1 H), 4.76-4.67 (m, 1 H), 4.61 (tt, J=4.1, 11.4 Hz, 1 H), 4.51 (s, 3 H), 4.18-4.09 (m, 1 H), 3.44-3.35 (m, 1 H), 2.90 (dt, J=2.5, 13.0 Hz, 1 H), 2.33-2.21 (m, 2 H), 2.20 (s, 3 H), 2.18-2.10 (m, 1 H), 2.10-1.98 (m, 1 H); MS (ESI): 457.37 [M+H]+; HPLC tR=2.23 min. 1-(4-{4-[7-amino-2-(2-methyl-2H-pyrazolo[3,4-c]pyridin-3-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)ethanone: 1H NMR (400 MHz, CD3OD): δ 9.85 (s, 1 H), 8.90 (d, J=6.6 Hz, 1 H), 8.39 (d, J=6.8 Hz, 1 H), 8.35 (s, 1 H), 8.07 (s, 1 H), 7.97 (s, 1 H), 7.91 (s, 1 H), 4.83 (s, 3 H), 4.73-4.65 (m, 1 H), 4.59 (tt, J=4.2, 11.4 Hz, 1 H), 4.16-4.07 (m, 1 H), 3.41-3.32 (m, 1 H), 2.88 (dt, J=2.5, 12.9 Hz, 1 H), 2.29-2.18 (m, 2 H), 2.17 (s, 3 H), 2.16-2.08 (m, 1 H), 2.08-1.95 (m, 1 H); MS (ESI): 457.37 [M+H]+; HPLC tR=2.14 min.