Stannane, tributyl(1-ethoxyethenyl)- → Methyl (8-acetylquinolin-2-yl)(phenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of Pd(PPh3)4 (60.8 mg, 0.053 mmol, Strem Chemicals, Newburyport, Mass.), tributyl(1-ethoxyvinyl)stannane (391 μl, 1.158 mmol, Sigma Aldrich), methyl (8-bromoquinolin-2-yl)(phenyl)carbamate (Example 46a; 376 mg, 1.053 mmol), and toluene (5.2 mL) were stirred under N2 at 100° C. for 20 h. Purification by column chromatography (silica gel: 0 to 10% EtOAc/hexanes followed by 70% EtOAc/hexanes) provided methyl (8-acetylquinolin-2-yl)(phenyl)carbamate, which was used without further purification in the next step. m/z (ESI, +ve) 349.1 (M+H)+.

Provenance & Evidence