HCID 89619215, compound → Tert-butyl 2-(4-methyl-5-pivalamidopyridin-2-yl)acetate

Participants

Reaction Steps

N-(6-bromo-4-methylpyridin-3-yl) pivalamide (0.644 g, 2.375 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl X-Phos (0.068 g, 0.143 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.065 g, 0.071 mmol) were dissolved in tetrahydrofuran (30 ml) then added 2-(tert-butoxy)-2-oxoethylzinc chloride (14.25 ml, 7.13 mmol). The mixture was placed into three tubes and microwaved at 100° C. for 1.5 hr. The reactions were poured into NH4Cl/brine solution and extracted with ETOAc (2×), dried over Na2SO4, filtered and concentrated. The residue was chromatographed through an 80 g ISCO Redi-sep column and eluted with ethyl acetate/hexane 1:2 to yield tert-butyl 2-(4-methyl-5-pivalamidopyridin-2-yl)acetate: LC-MS: M+1=307, 251 (M-56)

Provenance & Evidence