Triethylamine → (2S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-(4-fluorophenyl)-3-hydroxybut-1-ynyl)-3-methylnaphthalen-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (70 mg, 0.14 mmol) in THF (2 mL) was added 2-(4-fluorophenyl)but-3-yn-2-ol (46 mg, 0.28 mmol), CuI (5 mg, 0.028 mmol), Pd(PPh3)4 (17 mg, 0.014 mmol), and Et3N (80 μL, 0.57 mmol). The reaction mixture was stirred at 70° C. for 1 h. A saturated solution of NH4Cl was added. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes) to give the titled compound. 1H-NMR: 400 MHz, (CDCl3) δ: 7.56-7.66 (m, 4H), 7.29 (m, 6H), 6.97 (m, 2H), 5.02 (s, 1H), 4.06 (q, J=7 Hz, 2H). 2.54 (s, 3H), 1.76 (s, 3H), 1.10 (s, 9H), 0.80 (t, J=7 Hz, 3H).

Provenance & Evidence