Triethylamine → HCID 57828221, compound

Participants

Reaction Steps

A solution of (6-bromonaphthalen-2-yloxy)(tert-butyl)dimethylsilane (28, 3.4 g, 10.0 mmol), benzyl but-3-ynylcarbamate (17, 2.0 g, 10 mmole), and triethylamine (20 mL) in anhydrous THF (60 mL) pre-cooled to −78° C. was degassed with argon. The mixture was warmed to room temperature and dichlorobis(triphenylphosphine)palladium(II) (PdCl2(PPh3)2 (702 mg, 1 mmole) and CuI (381 mg, 2 mmole) were added rapidly in one portion under argon. The mixture was heated at 60° C. for 4 h, then at room temperature for 48 h. The reaction mixture was filtered through a plug of diatomaceous earth and the filtrate was partitioned between EtOAc (500 mL) and 1 N HCl (200 mL). The aqueous layer was separated and back-extracted with EtOAc (300 mL). The combined organic extracts were washed with water (300 mL) and brine (300 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (silical gel, 10:1 hexanes/EtOAc) to afford carbamate 29 (1.24 g, 37%) as a brown thick oil: 1H NMR (300 MHz, CDCl3) δ 7.83 (s, 1H), 7.65 (d, J=9.0 Hz, 1H), 7.60 (d, J=8.7 Hz, 1H), 7.39-7.29 (m, 6H), 7.13 (d, J=2.1 Hz, 1H), 7.07 (dd, J=8.7, 2.4 Hz, 1H), 5.17 (br s, 1H), 5.13 (s, 2H), 3.46 (q, J=6.3 Hz, 2H), 2.67 (t, J=6.3 Hz, 2H), 1.01 (s, 9H), 0.25 (s, 6H).

Provenance & Evidence