2-Fluoropyridine → HCID 67433925, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added (S)-tert-butyl 1-(6-fluoro-1H-benzo[d]imidazol-2-yl)ethylcarbamate (Prepared in Example 16, 0.5126 g, 1.835 mmol), N,N-Dimethylacetamide (4.08 mL), 2-fluoropyridine (0.189 mL, 2.202 mmol), and cesium carbonate (1.196 g, 3.67 mmol). The mixture was heated for 40 min in the microwave reactor (Temperature: 150° C. Pressure: 92˜94 psi, Power: 8˜10 W). At this time, the mixture was poured into EtOAc (100 mL), filtered and then concentrated on the high vacuum to remove most of the DMA. The residue was purified by silica gel column chromatography on a 40 g of Redi-Sep™ column using 0 to 20% gradient of EtOAc in hexane over 14 min, then 20% EtOAc in hexane for 14 min, then 20 to 50% gradient of EtOAc in hexane over 14 min, and then 50% EtOAc in hexane for 14 min as eluent to give a mixture of four isomer of two regioisomers and two stereoisomer of each regioisomer, 1-(6-fluoro-1-(pyridin-2-yl)-1H-benzo[d]imidazol-2-yl)ethanamine and 1-(5-fluoro-1-(pyridin-2-yl)-1H-benzo[d]imidazol-2-yl)ethanamine (0.1486 g, 0.580 mmol, 31.6% yield) as a yellow syrup: LC-MS (ESI) m/z 257.0 [M+H]+.

Provenance & Evidence