Palladium-catalyzed hydroxycarbonylation as the key step in the synthesis of a carbon-14 labeled Maxi-K channel blocker

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 53, Issue 7, 2010, Pages 511-516

  Simeone, Joseph P ^a   Braun, Matthew P ^a   Liu, Luping ^a   Natarajan, Swaminathan R ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Carbon 14; Carbonylation; Maxi K channel; Palladium catalyzed hydroxycarbonylation; 14C carbon monoxide

Indexed keywords

CARBON MONOXIDE; CATALYSIS; PALLADIUM COMPOUNDS; SODIUM COMPOUNDS;

A-CARBON; CARBON 14; CARBONYLATIONS; CHANNEL BLOCKERS; HYDROXYCARBONYLATION; MAXI-K CHANNEL; PALLADIUM-CATALYZED; PALLADIUM-CATALYZED HYDROXYCARBONYLATION; RADIOLABELED TRACERS; [ 14C]CARBON MONOXIDE;

CARBONYLATION;

1 BROMOPINACOLONE; 2 CHLORO 4,6 DIMETHOXYTRIAZINE; 4 IODOBROMOBENZENE; BROMINE DERIVATIVE; BROMOBENZENE; CARBON 14; CARBONYL DERIVATIVE; DI TERT BUTYL N,N DIETHYLPHOSPHORAMIDATE 1H TETRAZOLE; INDAZOLE DERIVATIVE; ISOTOPE; LARGE CONDUCTANCE CALCIUM ACTIVATED POTASSIUM CHANNEL; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; TERT BUTYL HYDROPEROXIDE; TRACER; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; ISOTOPE LABELING; REACTION ANALYSIS; SYNTHESIS;

EID: 77954361114     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1755     Document Type: Article

References (16)

1. M. L. Garcia, D.-M. Shen, G. J. Kaczorowski, Expert Opin. Ther. Patents 2007, 17, 831-842.
2. (a) W. O. Godtfredsen, PCT Int. Appl. 1989, WO89/10757;
3. (b) N. Sorgente, C. Bakhit, PCT Int. Appl. 1994, WO94/28900;
4. J. S. Adorante, E. Woldemussie, G. Ruiz, US Patent 5573758, 1996.
5. M. H. Chen, J. B. Doherty, L. Liu, S. Natarajan, R.M. Tynebor, PCT Int. Appl. WO2005/026128 A1, 2005.
6. J. L. Huston, T. H. Norris, J. Am. Chem. Soc. 1948, 70, 1968-1969.
7. C. S. Elmore, D. C. Dean, D. G. Melillo, J. Label. Compd. Radiopharm. 2000, 43, 1135-1144.
8. V. P. Baillargeon, J. K. Stille, J. Am. Chem. Soc. 1983, 105, 7175-7176.
9. H. Kotsuki, P. K. Datta, H. Suenaga, Synthesis 1996, 94, 470-472.
10. T. Okano, N. Harada, J. Kiji, Bull. Chem. Soc. Jpn. 1994, 67, 2329-2332.
11. For a review on this subject see: T. Morimoto, K. Kiyomi, Angew. Chem. Int. Ed. 2004, 43, 5580-5588.
12. (a) S. Cacchi, G. Fabrizi, A. Goggiamani, Org. Lett. 2003, 5, 4269-4272;
13. (b) P. Berger, A. Bessmernykh, J-C. Caille, S. Mignonac, Synthesis 2006, 18, 3106-3110.
14. S. Cacchi, G. Fabrizi, A. Goggiamani, J. Comb. Chem. 2004, 6, 692-694.
15. K. Kikukawa, T. Totoki, F. Wada, T. Matsuda, J. Organomet. Chem. 1984, 270, 283-287.
16. M. Falorni, G. Giacomelli, A. Porcheddu, M. Taddei, J. Org. Chem 1999, 64, 8962-8964.