2-Fluoropyridine → HCID 67019304, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-fluoropyridine (58.3 mg, 0.600 mmol), tert-butyl pyrrolidin-3-ylcarbamate (55.9 mg, 0.300 mmol), and TEA (84.0 μL, 0.600 mmol) in EtOH (1 mL) was heated at 120° C. for 30 min. The reaction was concentrated and the crude was purified by flash chromatography (12 g silica gel) using hexanes/EtOAc (0-50% over 10 min, flow rate 30 mL/min) to give Intermediate 48A (15 mg, 0.057 mmol, 19% yield) as a white solid. LCMS=264.3 [M+1], RT=1.11 min (Method H). 1H NMR (400 MHz, chloroform-d) δ ppm 8.15 (1H, dd, J=5.05, 1.01 Hz), 7.44 (1H, ddd, J=8.59, 6.95, 1.89 Hz), 6.55 (1H, dd, J=6.44, 5.18 Hz), 6.35 (1H, d, J=8.34 Hz), 4.74 (1H, br. s.), 4.35 (1H, br. s.), 3.71 (1H, dd, J=10.61, 6.06 Hz), 3.46-3.64 (2H, m), 3.34 (1H, dd, J=10.61, 4.04 Hz), 2.27 (1H, td, J=13.20, 7.45 Hz), 1.96 (1H, td, J=12.51, 5.56 Hz), 1.45 (9H, s).

Provenance & Evidence