Diisopropylethylamine → (S)-5-bromo-N-[methyl(oxido)phenyl--sulfanylidene]nicotinamide

To a solution of 5-bromonicotinic acid (1.21 g, 6.0 mmol), N,N-diisopropylethylamine (2.1 mL, 12.0 mmol), and (S)-(+)-S-methyl-S-phenylsulfoximine (931 mg, 6.0 mmol) in DMF (11.0 mL) cooled to 0° C. was treated with 1-benzotriazolyloxytripyrrolidinylphosphonium hexafluorophosphate (PyBOP) (3.43 g, 6.6 mmol). The reaction mixture was stirred 10 minutes, the ice bath removed, and the reaction continued at room temperature for 2 hours. The mixture was taken up in EtOAc and washed with H2O, Na2CO3 solution, brine, AcOH solution, H2O, Na2CO3 solution, brine, dried with anhydrous Na2SO4 and concentrated. The residual brown oil was purified by chromatography (silica gel, hexane/EtOAc). The product containing eluent was concentrated and then triturated with hexane to give the title compound as an off-white solid (1.88 g, 92%).

1. customthe ice bath removed
2. waitthe reaction continued at room temperature for 2 hours
3. washwashed with H2O, Na2CO3 solution, brine, AcOH solution, H2O, Na2CO3 solution, brine
4. dry with materialdried with anhydrous Na2SO4
5. concentrationconcentrated
6. customThe residual brown oil was purified by chromatography (silica gel, hexane/EtOAc)
7. additionThe product containing eluent
8. concentrationwas concentrated
9. customtriturated with hexane

ORD record

ord-cc230c367bb14ca7bc58f799a4df1643

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383825B2