Acrylonitrile → HCID 58765170, compound

Participants

Reaction Conditions

Reaction Steps

Acrylonitrile (10 mL of 1.52 M in 1,4-dioxane, 30.4 mmol) was added to methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (840 mg, 2.5 mmol) in a microwave vial. The vial was sealed and Triton® B (500 □L1.1□mol) was added via syringe. The vial was heated in a microwave apparatus for 1 hr at 100° C. The solution was cooled and poured to precipitate the crude product. The granular solid was collected, washed with water and dried. Recrystallization from ethanol gave the product as a colorless solid (696 mg, 74%). MS m/z 390 (MS+); 1H NMR (300 MHz, DMSO-D6) δ ppm 1.27–1.49 (m, 3 H) 1.60–2.01 (m, 7 H) 2.77–2.90 (m, 1 H) 2.98 (t, J=6.40 Hz, 2 H) 3.87 (s, 3 H) 4.62 (t, J=6.59 Hz, 2 H) 7.67 (dd, J=8.42, 1.46 Hz, 1 H) 7.83 (d, J=8.42 Hz, 1 H) 8.25 (s, 1 H).

Provenance & Evidence