Ethanol → Piperidine, 1-[2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-1,2-dioxoethyl]-4-(phenyl-2-pyridinylmethylene)-

Temperature

90 °C

To a solution of 1-[4-(1-bromo-1-phenyl-methylene)-piperidin-1-yl]-2-(4,7-dimethoxy-6-azaindol-3-yl)-ethane-1,2-dione (0.030 g, 0.062 mmole), pyridine-3-boronic acid (0.011 g, 0.093 mmol) in 4 mL of DME was added 2M sodium carbonate (0.12 mL, 0.24 mmol) and EtOH (1 mL) and the resulting mixture was degassed with a stream of Ar bubbles for 10 min. To this mixture was added Pd(dppf)2Cl2 (0.003 g, 5 mol %) and the reaction mixture was heated with stirring at 90° C. for 18 h. The cooled mixture was then filtered (C-18 cartridge and 0.45 μm filter), the residue was washed with MeOH and the filtrate was evaporated. Purification of the residual material by preparative HPLC afforded the title compound (0.011 g, 37%) as a light gray solid:

1. customthe resulting mixture was degassed with a stream of Ar bubbles for 10 min
2. additionTo this mixture was added Pd(dppf)2Cl2 (0.003 g, 5 mol %)
3. temperaturethe reaction mixture was heated
4. filtrationThe cooled mixture was then filtered
5. filtration(C-18 cartridge and 0.45 μm filter)
6. washthe residue was washed with MeOH
7. customthe filtrate was evaporated
8. customPurification of the residual material by preparative HPLC

ORD record

ord-8d1654c9d5434476a29c9086e98a3286

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348337B2