2-Bromo-4-methylpyridine → tert-Butyl 7-(4-methyl-2-pyridyl)-2,7-diazaspiro[4.5]decane-2-carboxylate

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Reaction Conditions

Reaction Steps

2-Bromo-4-methylpyridine (172 mg, 1 mmol) and tert-butyl 3,7-diazaspiro[4.5]decane-3-carboxylate (1 mmol, 240 mg) were dissolved in anhydrous dioxane (5 ml) under argon. Pd2(dba)3 (0.0165 mmol, 15 mg), Brettphos (30 mg, 0.0495 mmol), and sodium tert-butoxide (80 mg, 0.83 mmol) were added and the mixture was stirred at 100° C. overnight. Additional 2-bromo-4-methylpyridine (0.9 mmol, 100 μl) was added and stirring was continued at 100° C. overnight. The mixture was diluted with ethyl acetate, filtered through a plug of silica and concentrated under reduced pressure. The residue was purified by column chromatography (silica, gradient of 0 to 20% ethyl acetate in DCM) to yield 50 mg (0.15 mmol, 15%) MS(ESI) m/z=332.2 [M+1]+.

Provenance & Evidence