Triethylamine → HCID 66869797, compound

Participants

Reaction Steps

A microwave vial equipped with a flea stir bar was charged with 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-methylbut-3-yn-2-yl)carbamate (37 mg, 0.11 mmol), 1-bromo-4-fluorobenzene (39 mg, 0.22 mmol), Cul (2 mg, 0.011 mmol), Pd(PPh3)2Cl2 (4.7 mg, 0.007 mmol) and Et3N (1.5 mL). The mixture was sparged with N2 for 5 min and heated at 100 C for 2 h in the microwave. The mixture was concentrated and the residue was redissolved in EtOAc (90 mL), washed with 5% aq HCl (15 mL), satd aq NaHCO3 (15 mL) and brine (15 mL), and dried over Na2SO4. Removal of the solvent left an orange oil (46 mg) which was applied to a 2-g silica SPE cartridge and eluted sequentially with 0, 10, 25, 50 and 100% EtOAc in hexanes (15 mL of each) to give five fractions. Fractions 2 and 3 were pooled and concentrated to afford methyl 4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl(3-hydroxy-5-methyl-3-phenylhex-5-enyl)carbamate (35 mg, 73%) as an oil. LC-MS Method 1 tR=2.33 min, 406 (M−18).

Provenance & Evidence