Synthesis of diaryl acetates and oxindoles via a sequential VNS Ar-SNAr three-component coupling reaction

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4957-4960

  Lawrence, Nicholas J ^a,b   Davies, Christopher A ^a,b   Gray, Matthew ^c  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; OXINDOLE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CROSS COUPLING REACTION; QUANTUM YIELD; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

ACETATES; BENZENE DERIVATIVES; INDOLES; MOLECULAR STRUCTURE;

EID: 12344272714     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047890y     Document Type: Article

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27. NAr Reaction. Sodium hydride (60% dispersion in oil) (0.813 g, 20.3 mmol) was added to anhydrous DMF (5 mL) and the mixture flushed with nitrogen and cooled to °C. Chloroester 4 (8.13 mmol) and nitrobenzene (0.84 mL, 8.13 mmol) were dissolved in anhydrous DMF (5 mL) and added dropwise to the sodium hydride slurry. The reaction mixture was stirred at 0°C for 30 min and then allowed to warm to room temperature. The reaction mixture was then cooled back to 0°C using an ice-cooling bath. Aryl halide 5 (8.13 mmol) in anhydrous DMF (2 mL) was then added, and the resulting mixture was allowed to warm to room temperature and stirred for a further 2 h. The reaction mixture was poured onto ice/hydrochloric acid (50 mL, 1 M solution) and extracted with dichloromethane (3 x 30 mL). The combined organic extracts were washed well with distilled water (5 x 50 mL) and then saturated aqueous sodium bicarbonate solution (3 x 50 mL) and dried (magnesium sulfate), and the solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography
28. 13C NMR, MS, IR) support the product assignment.
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