Tert-butyl 3-bromo-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)benzoate → Tert-butyl 3-(5-methylpyridin-2-yl)-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-bromo-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)benzoate (1.42 g, 3.88 mmol) and bis(tri-tert-butylphosphine)palladium(0) (59.0 mg, 0.12 mmol) in dioxane (20 mL) was added 5-methyl-2-pyridylzinc bromide (0.5 M in THF; 15.5 mL, 7.75 mmol). The reaction mixture was heated to 70° C. After 1 h, the reaction was cooled to ambient temperature and the solvent was evaporated. Saturated aqueous sodium potassium tartrate was adde and the mixture was extracted with ethyl acetae (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate) gave the title compound (1.42 g). MS 379.2 (M+1).

Provenance & Evidence