Triethylamine → 1-[3-(2-Methoxy-4-nitro-phenyl)-prop-2-ynyl]-pyrrolidine

Participants

Reaction Steps

Dissolve 1-iodo-2-methoxy-4-nitro-benzene (618 mg, 2.21 mmol) in acetonitrile (10 mL) and treat sequentially with 1-prop-2-ynyl-pyrrolidine (352 mg, 3.22 mmol), Et3N (2 mL), CuI (77 mg, 0.404 mmol) and Pd(PPh3)4 (360 mg, 0.311 mmol). Stir the mixture at room temperature for 3 h, then dilute with EtOAc (50 mL) and wash with saturated NaHCO3 (30 mL). Dry, filter and concentrate the organic solution. Purify the crude material by flash chromatography, using a linear gradient of 50% EtOAc/hexanes to 100% EtOAc, to give the title compound as an orange oil (292 mg, 51%). MS (ES+) 261.1 (M+1)+. 1H NMR (400 MHz, CDCl3) δ: 7.77 (dd, 1H, J=8.3, 2.2 Hz), 7.70 (d, 1H, J=2.2 Hz), 7.50 (d, 1H, J=8.3 Hz), 3.95 (s, 3H), 3.72 (s, 2H), 2.75-2.70 (m, 4H), 1.87-1.83 (m, 4H).

Provenance & Evidence