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

Participants

Reaction Steps

A mixture of 1-{4-[4-(7-amino-2-chlorofuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (15.0 mg, 0.0417 mmol), 4-fluoro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzothiazole (23.3 mg, 0.0824 mmol), Pd(PPh3)4 (4.82 mg, 0.00417 mmol), potassium carbonate (17.3 mg, 0.125 mmol) and 4:1 dioxane:H2O (1 mL) was heated in a microwave reactor at 110° C. for 40 min. The crude reaction mixture was purified by preparative HPLC to afford 3.8 mg (19%) the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 1.97-2.15 (m, 2 H), 2.19 (s, 3 H), 2.19-2.30 (m, 2 H), 2.88 (td, J=13.0, 2.8 Hz, 1 H), 3.33-3.40 (m, 1 H), 4.07-4.16 (m, 1 H), 4.54 (tt, J=11.5, 4.2 Hz, 1 H), 4.65-4.74 (m, 1 H), 7.27 (dd, J=9.3, 8.3 Hz, 1 H), 7.41 (s, 1 H), 7.83 (s, 1H), 7.87 (s, 1 H), 8.09 (s, 1H), 8.20 (s, 2 H), 8.22 (dd, J=8.3, 4.5 Hz, 1 H), 9.06 (s, 1 H); MS (ESI): 477.13 [M+H]+; HPLC tR=1.10 min (TOF: polar—3 min).

Provenance & Evidence