Acrylonitrile → HCID 16072743, compound

Participants

Reaction Conditions

Reaction Steps

Acrylonitrile (2 mL of 1.52 M in 1,4-dioxane, 3.04 mmol) was added to methyl 3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate (200 mg, 0.55 mmol) in a microwave vial. The vial was sealed and Triton® B (50 μL, 0.11 μmol) was added via syringe. The vial was heated in a microwave apparatus for 1 hr at 100° C. The solution was concentrated and the residue dissolved in methylene chloride. The solution was applied to a silica gel thick layer plate. The plated was eluted with hexanes-ethyl acetate (8:2). The product containing band was extracted with methylene chloride-methanol (3×). The combined extracts were concentrated and the residue recrystallized from methanol to afford the titled compound as a tan solid. MS m/z 397 (MH); 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.16-2.25 (m, 10 H) 2.90-3.10 (m, 1 H) 3.20-3.34 (m, 1 H) 3.60-3.75 (m, 1H) 3.95 (s, 3 H) 7.28-7.49 (m, 4 H) 7.76 (s, 1 H) 7.86-7.97 (m, 2 H) 8.13 (s, 1 H).

Provenance & Evidence