Potassium Carbonate → HCID 86625191, compound

Participants

Reaction Steps

To (1S,4S)-2-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-2,5-diazabicyclo-[2.2.1]heptane (0.40 g, 1.2 mmol) and K2CO3 (0.38 g, 2.8 mmol) in DMF (10 mL) was added 1-iodo-2-fluoroethane (0.26 g, 1.5 mmol), and the reaction was stirred overnight. More 1-iodo-2-fluoroethane (50 mg, 0.29 mmol) was added, and the solution stirred an additional 4 h. The solvent was removed under vacuum, and the residue was taken up in DCM. Silica was added, and the solvent removed under vacuum. Silica gel chromatography provided the title compound of step C as a yellow oil (230 mg, 0.61 mmol, 49% yield). 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=9.3 Hz, 1H), 6.38 (dd, J=9.3, 2.4 Hz, 1H), 6.27 (d, J=2.4 Hz, 1H), 4.58-4.39 (m, 2H), 3.91 (s, 3H), 3.82-3.73 (m, 2H), 3.51 (br s, 1H), 3.34 (br s, 1H), 3.08-2.98 (m, 2H), 2.96-2.53 (m, 7H), 1.96-1.65 (m, 4H), 1.59-1.46 (m, 2H).

Provenance & Evidence