1-Fluoro-2-(2-nitroethenyl)benzene → HCID 15983335, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-{3-Dimethoxymethyl-4-[1-(2-fluoro-phenyl)-2-nitro-ethyl]-phenoxy}-propyl)-piperidine. A −78° C. solution of 5-bromo-4-dimethoxymethyl-2-(3-piperidin-1-yl-propoxy)-pyridine (359 mg, 0.962 mmol) in THF (8 mL) was treated with n-BuLi (2.5 M in hexanes; 0.4 mL). After 20 min at −78° C., the mixture was treated with a solution of 1-fluoro-2-(2-nitro-vinyl)-benzene (171 mg, 1.02 mmol) in THF (5 mL). After 20 min at −78° C., the mixture was treated with acetic acid (1 mL) and was allowed to warm to 0° C. The mixture was concentrated and the residue was chromatographed (SiO2; 1-10% 2 M NH3 in MeOH/DCM) to give the title compound (285 mg, 64%) as an oil. MS (ESI): mass calcd. for C24H32FN3O5, 461.23; m/z found, 462.5 [M+H]+. 1H NMR (CDCl3): 8.03 (s, 1H), 7.30-7.24 (m, 2H), 7.15-7.03 (m, 2H), 6.95 (s, 1H), 5.55 (t, 8.2, 1H), 5.43 (s, 1H), 5.02-4.92 (m, 2H), 4.34-4.27 (m 2H), 3.35 (s, 3H), 3.27 (s, 3H), 2.55-2.42 (m, 6H), 2.05-1.95 (m, 2H), 1.69-1.60 (m, 4H), 1.49-1.42 (m, 2H).

Provenance & Evidence