1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-[3-Cyclopropyl-2-(2,6-dichloro-pyridin-4-yl)-3H-imidazol-4-yl]-2-methyl-acrylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

3-cyclopropyl-2-(2,6-dichloro-pyridin-4-yl)-3H-imidazole-4-carbaldehyde (1.48 g, 5.25 mmol), triethyl-2-phosphonopropionate (1.46 ml, 6.83 mmol) and DBU(1.02 ml, 6.83 mmol) were dissolved in acetonitrile (20 ml). After stirring at 78° C. o.n. the reaction mixture was cooled to r.t, diluted with water and extracted with DCM. The combined organic phase was dried (Na2SO4), filtered and concentrated in-vacuo. The crude was purified on silica gel using 6% EA in DCM, and the isolated residue was triturated with hex. to isolate the title compound (1.66 g, 86%). 1H-NMR: 7.86 (m, 1H), 7.75 (d, 2H), 7.43 (s, 1H), 4.34 (q, 2H), 3.45 (m, 1H), 2.19 (s, 3H), 1.39 (t, 3H), 1.29 (m, 2H), 0.78 (m, 2H).

Provenance & Evidence