Sodium hydride → 3-Bromo-5-(1,1-dioxo-isothiazolidin-2-ylmethyl)-pyridine

HRID 2407432Notes

Reaction equation

[O:1]=[S:2]1(=[O:7])[CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].Cl.[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18]Cl)[CH:17]=1>CN(C=O)C>[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][N:3]2[CH2:4][CH2:5][CH2:6][S:2]2(=[O:7])=[O:1])[CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 40 mL scintillation vial was charged with 1,1-dioxo-isothiazolidine (115 mg, 0.949 mmol) and DMF (3 mL). The reaction mixture was cooled to 0° C. and sodium hydride (95 mg, 2.373 mmol) was added. The reaction was left to stir at room temperature for 20 min followed by the addition of 3-bromo-5-(chloromethyl)pyridine hydrochloride (277 mg, 1.139 mmol). The reaction was stirred at room temperature for 3 h, then quenched with water and extracted with ethyl acetate. The organic layer was washed with water twice, dried over sodium sulfate and concentrated in vacuo. The crude was purified by silica gel flash chromatography using heptane-ethyl acetate (60-40, v/v) to afford 3-bromo-5-(1,1-dioxo-isothiazolidin-2-ylmethyl)-pyridine as a colorless oil. MS (ESI) m/z 292.9 (M+H)+

Workup

waitThe reaction was left
stirringThe reaction was stirred at room temperature for 3 h
customquenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with water twice
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-31a8b31e9dda47a399d3da355263fdee
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809545B2

Reaction notes

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