Benzylamine → HCID 67163569, compound

Participants

Reaction Conditions

Reaction Steps

A flame dried Schlenk flask was charged with 1-[(2R,4S,5R)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl]-4-chloro-1H-pyrrolo[3,2-c]pyridine (0.343 g, 0.690 mmol), 1,4 dioxane (1.40 mL), benzylamine (0.226 mL, 2.07 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.0126 g, 0.0138 mmol), 2-(dicyclohexylphosphino)biphenyl (0.00686 g, 0.0196 mmol), and sodium tert-butoxide (0.186 g, 1.93 mmol). The tube purged with N2 (3×), sealed and the mixture was heated at 95° C. overnight. The reaction mixture was cooled to r.t., diluted with CH2Cl2 (20 mL) and washed with water (20 mL). The aq layer was extracted with CH2Cl2 (3×20 mL) and the combined organics were dried (Na2SO4), filtered, and concentrated. The crude oil was purified by flash chromatography (10 to 40% EtOAc/hexanes) to give the title compound as a light yellow foam (0.313 g, 28%).

Provenance & Evidence