Tetrahydrofuran → HCID 58790056, compound

Participants

Reaction Steps

To a solution of bromide 50 (3.0 g, 8.13 mmol) in THF (40 ml) was added 4-(prop-2-ynyl)dimethylamine (2.70 g, 32.5 mmol) [H-W. Tsou, et. al. J. Med. Chem., 2001, 44, 2719-2734], triethylamine (2.05 g, 2.5 eq, 20.3 mmol), CuI (154 mg, 0.1 eq, 0.813 mmol) and Pd(PPh3)2Cl2 (319 mg, 0.056 eq, 0.046 mmol). The reaction mixture was degassed with nitrogen and refluxed for 2 hrs, cooled to room temperature and adsorbed onto silica. Purification by column chromatography (eluent EtOAc to 20% MeOH in EtOAc) afforded 69 as a yellow solid (2.5 g, 83% yield). 1H NMR (DMSO-d6) δ (ppm): 8.65 (m, 1H), 8.48 (dd, J=2.74 and 10.56 Hz, 1H), 8.22 (m, 1H), 7.85 (s, 1H), 7.75 (m, 1H), 6.98 (d, J=5.28 Hz, 1H), 3.59 (s, 2H), 2.26 (s, 6H).

Provenance & Evidence