Dimethylacetamide → HCID 67199950, compound

Participants

Reaction Conditions

Reaction Steps

To 5-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]-6-fluoro-N-[(5-fluoro-6-methoxy-3-pyridyl)methyl]pyridin-2-amine (125 mg, 0.27 mmol) was added 2 mL of N,N-dimethylacetamide. The mixture suspension was degassed by bubbling with argon. To this suspension was added Zinc (5 mg, 0.08 mmol), 11,1′-Bis(diphenylphosphino)ferrocene (6 mg, 0.01 mmol), Zinc Cyanide (0.01 ml, 0.19 mmol), and Tris(dibenzylideneacetone)dipalladium (0) (7 mg, 0.01 mmol) at room temperature under argon. The mixture was heated to 120° C. for 2 hrs and cooled to room temperature. The reaction mixture was extracted with ethyl acetate and water (+saturated sodium chloride). The organic layer was washed with water and brine, dried by MgSO4. The volatiles were removed under vacuum. The residue was suspended in acetonitrile and sonicated for 45 mins. The precipitate was collected by filtration and washed with acetonitrile. A tan solid was obtained (98 mg, 88.8% yield). LC-MS showed one major peak with 98.6% purity. The structure of the product is confirmed by H1-NMR (DMSO-d6). MS (ESI) [M+H]+=406.9.

Provenance & Evidence