Triethylamine → HCID 57791874, compound

Participants

Reaction Steps

A suspension of 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.55 g, 2.261 mmol) in dry CH2Cl2:1,4-dioxane (15 mL, 2:1) was treated with triethylamine (0.636 mL, 4.52 mmol), followed by 2-bromoethanol (0.176 mL, 2.487 mmol) at room temperature. Only starting material was observed after stirring for 4 h at room temperature. The reaction was then refluxed for 24 h. The reaction was brought to room temperature, diluted with 1 N NaOH solution (25 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain 2-(4-(5-nitro-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanol (0.24 g, 36.9%) as a dark yellow solid. 1H NMR (DMSO-d6) δ 11.86 (s, 1H), 8.68 (d, 1H, J=2.1 Hz), 8.01 (dd, 1H, J=2.4, 9.0 Hz), 7.65 (s, 1H), 7.55 (d, 1H, J=9.0 Hz), 6.16 (s, 1H), 4.42 (t, 1H, J=5.4 Hz), 3.56 (q, 2H), 3.18 (t, 2H, J=6.3 Hz), 2.69 (t, 2H, J=5.4 Hz), 2.54-2.50 (m, 4H); ESI-MS (m/z, %): 288 (MH+, 100).

Provenance & Evidence