Triethylamine → 6'-(Cyclopropylethynyl)-5''-methyl-3'H-dispiro[cyclobutane-1, 2'-indene-1',2''-imidazol]-4''-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 6′-bromo-5″-methyl-3′H-dispiro[cyclobutane-1,2′-indene-1′,2″-imidazol]-4″-amine (Example 54, 0.10 g, 0.31 mmol) in DMF (10 mL) under argon was added ethynylcyclo-propane (0.031 g, 0.47 mmol), tetrakis(triphenylphosphine)palladium(0) (0.036 g, 0.03 mmol) and triethylamine (1.31 mL, 9.43 mmol). The reaction mixture was stirred at r.t. for 5 min before addition of cuprous iodide (8.98 mg, 0.05 mmol). The reaction mixture was stirred overnight at 65° C. The reaction mixture was partitioned between sat aq. NaHCO3 and EtOAc. The organic phase was dried over MgSO4 and concentrated to give a crude product which was purified by preparative chromatography to afford the title compound (0.046 g, 48% yield): 1 H NMR (500 MHz, DMSO-d6) δ ppm 0.60-0.73 (m, 2 H), 0.77-0.89 (m, 2 H), 1.46 (tt, 1 H), 1.50-1.65 (m, 4 H), 1.72-1.85 (m, 1 H), 2.08-2.16 (m, 1 H), 2.18 (s, 3 H), 3.07-3.23 (m, 2 H), 6.54 (d, 1 H), 6.60 (s, 2 H), 7.16 (dd, 1 H), 7.20-7.27 (m, 1 H); MS (ES+) m/z 304 [M+H]+.

Provenance & Evidence