N-Fluorobenzenesulfonimide → HCID 90074665, compound

Lithium bis(trimethylsilyl)amide (0.45 mL, 1M in tetrahydrofuran, 0.45 mmol) is added to a solution of commercially available 5-bromo-2-(methylsulfonylmethyl)pyridine (102 mg, 0.408 mmol) in tetrahydrofuran (5 mL) at −78° C. After 45 minutes N-Fluorodibenzenesulfonamide (156 mg) in tetrahydrofuran (10 mL) is added to the reaction mixture at −78° C. over 5 minutes. After stirring for 20 minutes the reaction is quenched with water (10 mL) and ethyl acetate(10 mL). The reaction mixture is partitioned between saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (10 mL). The combined organic layers are washed with brine and concentrated to give the crude product, which is purified by flash column chromatography eluting from neat hexane to neat ethyl acetate to give the title compound (50 mg): m/z (Cl) 268 (M+H).

1. customis quenched with water (10 mL) and ethyl acetate(10 mL)
2. customThe reaction mixture is partitioned between saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (10 mL)
3. washThe combined organic layers are washed with brine
4. concentrationconcentrated
5. customto give the crude product, which
6. customis purified by flash column chromatography
7. washeluting from neat hexane to neat ethyl acetate

ORD record

ord-e87dcc581d9c466191d62b576098a0f9

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206126B2