Potassium Carbonate → 1-(4-{4-[7-amino-2-([1,2]thiazolo[4,5-c]pyridin-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 4-iodo-2-([1,2]thiazolo[4,5-c]pyridin-7-yl)furo[2,3-c]pyridin-7-amine (7.0 mg, 0.018 mmol), 1-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (8.5 mg, 0.027 mmol), Pd(PPh3)4 (1.0 mg, 0.00089 mmol), potassium carbonate (7.4 mg, 0.053 mmol) and 4:1 dioxane:water (1 mL) was heated in a microwave reactor at 85° C. for 20 min. The solution was used directly for HPLC purification, and the fractions containing the pure product were concentrated in vacuo to afford 3.1 mg (38%) of the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 2.03-2.16 (m, 2 H), 2.19 (s, 3 H), 2.20-2.31 (m, 2 H), 2.88 (td, J=12.9, 2.7 Hz, 1 H), 3.34-3.41 (m, 1 H), 4.08-4.17 (m, 1 H), 4.55 (tdd, J=11.4, 11.4, 4.2, 4.0 Hz, 1 H), 4.67-4.75 (m, 1 H), 7.72 (s, 1 H), 7.89 (s, 1 H), 7.92 (s, 1 H), 8.15 (s, 1 H), 8.16 (s, 2 H), 9.23 (s, 1 H), 9.28 (s, 1 H), 9.44 (s, 1 H); MS (ESI): 460.63 [M+H]+; HPLC tR=0.56 min (TOF: polar—3 min).

Provenance & Evidence