A new approach to the solid-phase Suzuki coupling reaction

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1197-1200

  Piettre, Serge R ^a   Baltzer, Sylvie ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0031575574     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00063-4     Document Type: Article

References (32)

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18. 6. A somewhat different strategy using polymer-supported tin reagent has also been developed; see: Kuhn H.; Neumann, W. P. Synlett 1994, 123-124.
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23. 10. Fmoc-Rink amide resin (Novabiochem, 0.45 mmol/g) was deprotected (50% piperidine in DMF) and coupled with the required iodobenzoic acid (DIC (4 eq)/HOBT (4 eq)) in DMF (negative to Kaiser ninhydrin test). Incorporation of the acid on the resin was verified by cleavage from the polymer; 96(± 2)% of the theoretical amount of iodobenzoic acid was consistently recovered.
24. 1H-NMR spectroscopy) and no iodobenzoic acid could be detected by HPLC.
25. 12. For example, potassium or cesium carbonate were found to be equally effective, while triethylamine promoted a much lower conversion (20-25%) of boronate 3 into the bisaryl derivative. In addition, longer reaction time with potassium phosphate resulted in lower isolated yields.
26. 13. The lower reaction rate is probably due to steric hindrance generated by the ortho substitution (see reference 14). We found that about 50% of polymer-bound o-iodobenzoate remained unconsumed after 20 hours of heating, while 48 hours of heating led to a 71% consumption of the iodo derivative. Similarly, The Suzuki reaction was much slower than with boronates 4a and 4b.
27. 1H-NMR spectroscopy; one unidentified by-product), but with a mass recovery of 74%.
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29. 16. All compounds described in the paper had analytical data in accordance with the structures.
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