N,N,N',N'-Tetramethylethylenediamine → Benzyl [(3S)-1-(3-cyano-5-nitropyridin-4-yl)piperidin-3-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl [(3S)-1-(3-bromo-5-nitropyridin-4-yl)piperidin-3-yl]carbamate (0.082 g, 0.19 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.0097 g, 0.0094 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.0109 g, 0.0188 mmol), zinc cyanide (0.066 g, 0.56 mmol), N,N,N′,N′-tetramethylethylenediamine (0.0114 mL, 0.0755 mmol) in DMF (1.40 mL) was in a vial was deoxygenated. The vial was purged with nitrogen several times, then sealed. The reaction mixture was heated in the sealed vial at 140° C. under microwave irradiation for 10 min. After cooling to ambient temperature, the crude reaction mixture was filtered through a pad of diatomaceous earth and the inorganics were washed thoroughly with EtOAc. The filtrate was diluted EtOAc (40 mL) and water (3 mL). The layers were separated and the organic layer was washed with water (3×3 mL). The combined aqueous phases were extracted with EtOAc (3 mL). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the sub-title compound (0.065 g). The crude product was used without further purification in the subsequent reaction. LCMS (ESI) calc. for C19H20N5O4 [M+H]+: m/z=382.1. found 382.0.

Provenance & Evidence