Tributylvinyltin → HCID 10221196, compound

Participants

Reaction Conditions

Reaction Steps

3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromo-6-chloro-pyridine from Example 69a (0.95 g, 2.4 mmol) and tetrakis(triphenylphophino) palladium (0.14 g, 0.12 mmol) were dissolved in toluene (50 mL) and degassed with nitrogen gas for 5 min. Vinyl tributyltin (0.78 mL, 2.67 mmol) was added and the mixture was heated to 90° C. for 1 day. The reaction solvent was evaporated and the crude residue was chromatographed (silica gel; hexanes/EtOAc, 4:1) to provide the title compound (0.69 g, 2.04 mmol, 85%). TLC Rf 0.3 (4:1 hexanes/EtOAc). MS (CI/NH3) m/z 339 (M+H)+. Continued elution provided a minor amount of 5,6-diethenylpyridine (0.044 g, 0.13 mmol, 5.5%): TLC Rf 0.25 (4:1 hexanes/EtOAc); MS (CI/NH3) m/e 331 (M+H)+.

Provenance & Evidence