Triethylamine → (S)-6-amino-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide

To a degassed solution containing (S)-6-amino-5-iodo-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamide (345 mg, 0.86 mmol) in 6.0 mL DMF at room temperature was added triethylamine (0.36 mL, 2.6 mmol), trimethylsilylacetylene (0.24 mL, 1.7 mmol), dichlorobis(triphenylphosphine)palladium(II) (60 mg, 0.09 mmol), and copper(I)iodide (16 mg, 0.09 mmol). After stirring at room temperature for 1 hour, the reaction was partitioned between EtOAc and H2O. The EtOAc layer was washed with saturated NaHCO3, brine, dried with anhydrous Na2SO4 and rotary evaporated. Then added 30 mL ethyl ether to the dark oil, filtered to remove the dark precipitate. The organic extracts were concentrated and the residue was purified by chromatography (silica gel, ethyl ether/EtOAc) to the title compound as a tan foam (317 mg, 99%).

1. customthe reaction was partitioned between EtOAc and H2O
2. washThe EtOAc layer was washed with saturated NaHCO3, brine
3. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
4. additionThen added 30 mL ethyl ether to the dark oil
5. filtrationfiltered
6. customto remove the dark precipitate
7. concentrationThe organic extracts were concentrated
8. customthe residue was purified by chromatography (silica gel, ethyl ether/EtOAc) to the title compound as a tan foam (317 mg, 99%)

ORDレコード

ord-f2e31e89c7874c23b642735b1d55eff2

出典データセット

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08143410B2