Triethylamine → 5-{2-Benzyloxy-4-[(E)-2-(6-methoxypyridin-2-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2-benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (Example 81, step A) (75 mg, 0.17 mmol) in acetonitrile (2 mL), in a pressure vessel, is added 2-bromo-6-methoxypyridine (32 mg, 0.17 mmol), NEt3 (0.05 mL, 0.34 mmol), Pd(OAc)2 (8 mg, 0.034 mmol), and 2-(di-t-butylphosphino)biphenyl (20 mg, 0.068 mmol). The vessel is sealed and stirred at 100° C. for 18 h. The reaction is cooled to RT and filtered through Celite. The solvent is removed under reduced pressure and the crude material purified by column chromatography using a gradient of 0-35% EtOAc/hexanes as eluent to afford the title compound as a yellow oil: (M+H)+=552.

Provenance & Evidence