Triethylamine → HCID 67126145, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(5-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (100 mg, 0.20 mmol) and N,N-dimethylprop-2-yn-1-amine (0.065 mL, 0.61 mmol) in anhydrous tetrahydrofuran was added copper iodide (8 mg, 0.04 mmol) and PdCl2(PPh3)2 (14 mg, 0.02 mmol). The reaction was heated to 100° C. overnight. After cooling to room temperature the reaction was charged with PdCl2(PPh3)2 (14 mg, 0.02 mmol), copper iodide (8 mg, 0.04 mmol), N,N-dimethylprop-2-yn-1-amine (0.065 mL, 0.61 mmol) and triethylamine (1 mL). The reaction was heated to 100° C. overnight. To the reaction was then added N,N-dimethylprop-2-yn-1-amine (0.065 mL, 0.61 mmol) and heated to 100° C. overnight. The crude reaction mixture was absorbed onto silica gel and purified by flash column chromatography (silica gel, ethyl acetate/hexanes, methanol/ethyl acetate) to give a yellow oil (6.5 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C30H35ClNO3: 492.22; found: 492.15.

Provenance & Evidence