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

Participants

Reaction Conditions

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 (45 mg, 0.13 mmol), [1-(tert-butoxycarbonyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]boronic acid (65 mg, 0.26 mmol), Na2CO3 (55 mg, 0.52 mmol) and Pd(PPh3)4 (10 mg, 0.0087 mmol) in 4:1 dioxane:water (5 mL) was degassed with N2 for 1 min, and then heated to 120° C. in a microwave reactor for 30 min. The mixture was filtered and the filtrate was purified by preparative TLC (5:1 DCM:MeOH) to afford 16 mg (29%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.79 (s, 1H), 8.28-8.27 (m, 3H), 8.16 (s, 1H), 7.93 (s, 1H), 7.86 (s, 1H), 7.25 (s, 1H), 4.71-4.68 (m, 1H), 4.57-4.54 (m, 1H), 4.13-4.09 (m, 1H), 3.37 (m, 1H), 2.85 (m, 1H), 2.21 (m, 1H), 2.13 (s, 3H), 1.95 (m, 1H); MS (ESI): 442.1 [M+H]+; HPLC tR=2.08 min (ZQ3: polar—4 min).

Provenance & Evidence