1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68453166, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-bromo-1,3-thiazole-5-carboxylate (2.101 g, 9.46 mmol), (3S)-3-[2-(trifluoromethyl)phenoxy]pyrrolidine (2 g, 8.7 mmol) and DBU (2.7 mL, 17.9 mmol) in dioxane (30 mL) was heated at 80° C. for 24 h. After cooling, the mixture was diluted with water and extracted twice with EtOAc. The combined EtOAc extracts were washed with water, dried and concentrated. Combi-Flash chromatography (120 g, 40-80% EtOAc in hexanes in 20 min, 70 mL/min, 25 mL/fraction) gave the title compound as a white solid. 1H NMR (400 MHz, acetone-d6): δ 7.84 (s, 1 H), 7.67 (m, 2 H), 7.41 (d, 1 H), 7.17 (t, 1 H), 5.51 (s, 1 H), 3.95 (m, 1 H), 3.80-3.65 (m, 6 H), 2.60-2.46 (m, 2 H).

Provenance & Evidence