Palladium(0)-mediated rapid methylation and fluoromethylation on carbon frameworks by reacting methyl and fluoromethyl iodide with aryl and alkenyl boronic acid esters: Useful for the synthesis of [11C]CH 3-C-and [18F]FCH2-C-containing PET tracers (PET = positron emission tomography)

Chemistry - A European Journal

Volumn 15, Issue 16, 2009, Pages 4165-4171

  Doi, Hisashi ^a   Ban, Ikuya ^b   Nonoyama, Akihito ^b   Sumi, Kengo ^b   Kuang, Chunxiang ^b   Hosoya, Takamitsu ^c   Tsukada, Hideo ^d   Suzuki, Masaaki ^a,b  

^a RIKEN   (Japan)

^b GIFU UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^d CENTRAL RESEARCH LABORATORY   (Japan)

Author keywords

Boron; C C coupling; Isotopic labeling; Palladium; PET (positron emission tomography)

Indexed keywords

ALKENYL; BENZYLIDENE ACETONES; BORONIC ACIDS; C - C COUPLING; CARBON FRAMEWORKS; COMPLEMENTARY METHODS; FLUOROMETHYLATION; HIGH YIELDS; ISOTOPIC LABELING; METHYL IODIDES; PET (POSITRON EMISSION TOMOGRAPHY); PET TRACERS; PINACOL;

ALKYLATION; BORON; BORON COMPOUNDS; DIAGNOSTIC RADIOGRAPHY; ELECTRONS; ESTERS; ISOTOPES; LABELING; METHYLATION; PALLADIUM; POSITRON ANNIHILATION SPECTROSCOPY; POSITRONS; SYNTHESIS (CHEMICAL);

POSITRON EMISSION TOMOGRAPHY;

BORON DERIVATIVE; CARBON; DIAGNOSTIC AGENT; FLUORINE; IODINATED HYDROCARBON; PALLADIUM; RADIOPHARMACEUTICAL AGENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHYLATION; POSITRON EMISSION TOMOGRAPHY; SYNTHESIS;

BORON COMPOUNDS; CARBON RADIOISOTOPES; COMBINATORIAL CHEMISTRY TECHNIQUES; FLUORINE RADIOISOTOPES; HYDROCARBONS, IODINATED; METHYLATION; MOLECULAR STRUCTURE; PALLADIUM; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS;

EID: 65349175070     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801974     Document Type: Article

References (63)

1. a) M. E. Phelps, PET: Molecular Imaging and Its Biological Applications, Springer, New York, Berlin, Heidelberg, 2004.
2. b) Positron Emission Tomography (Eds.: D. L. Bailey, D. W. Townsend, P. E. Valk, M. N. Maisey), Basic Science, Springer. New York, Berlin, Heidelberg, 2005;
3. c) J. S. Fowler, A. P. Wolf, Acc. Chem. Res. 1997, 30, 181-188;
4. d) S. M. Ametamey, M. Honer, P. A. Schubiger, Chem. Rev. 2008, 108, 1501-1516.
5. a) G. Lappin, R. C. Garner, Nat. Rev. Drug Discovery 2003, 2, 233-240;
6. b) M. Bergström, A. Grahnén, B. Långström, Eur. J. Clin. Pharmacol. 2003, 59, 357-366;
7. c) The European Medicines Agency, Evaluation of Medicines for Human Use, Position paper on non-clinical safety studies to support clinical trials with a single microdose, CPMP/SWP/2599/02/Revl, 23 June 2004;
8. d) U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research, Guidance for Industry, Investigators, and Reviewers, Exploratory IND Studies, January 2006;
9. e) Japan's response to microdosing study. Notification No. 0603001, 3 June 2008; Guidance for the Conduct of Microdoing Clinical Trials, Evaluation and Licensing Division, Pharmaceutical and Food Safety Bureau, Ministry of Health, Labour and Walfare, Japan.
10. a) PET Chemistry, The Driving Force in Molecular Imaging (Eds.:P. A. Schubiger, L. Lehmann, M. Friebe), Springer, New York. Berlin, Heidelberg, 2007;
11. b) M. Allard, E. Fouquet, D. James. M. Szlosek-Pinaud, Curr. Med. Chem. 2008, 15, 235-277;
12. c) L. Cai. S. Lu, V. W. Pike. Eur. J. Org. Chem. 2008, 2853-2873.
13. a) M. Suzuki, H. Doi, M. Björkman, Y. Andersson, B. Långström, Y. Watanabe, R. Noyori, Chem. Eur. J. 1997, 3, 2039-2042:
14. b) M. Suzuki, R. Noyori, B. Långström, Y. Watanabe, Bull. Chem. Soc. Jpn. 2000, 73, 1053-1070:
15. c) M. Suzuki. H. Doi, K. Kato, M. Björkman, B. Långström, Y. Watanabe, R. Noyori, Tetrahedron 2000, 56, 8263-8273;
16. d) M. Björkman, H. Doi. B. Resul, M. Suzuki. R. Noyori, Y. Watanabe, B. Långström. J. Labelled Compd. Radiopharm. 2000, 43, 1327-1334;
17. e) T. Hosoya, M. Wakao, Y. Kondo, H. Doi. M. Suzuki, Org. Biomol. Chem. 2004, 2, 24-27:
18. f) M. Suzuki, H. Doi, T. Hosoya. B. Långström, Y. Watanabe, TrAC, Trends Anal. Chem. 2004, 23, 595-607;
19. g) T. Hosoya, K. Sumi, H. Doi. M. Wakao, M. Suzuki, Org. Biomol. Chem. 2006, 4, 410-415;
20. h) R. Noyori, Angew. Chem. 2002, 114, 2108-2123;
21. Angew. Chem. Int. Ed.2002, 41, 2008-2022.
22. a) M. Suzuki. K. Kato, R. Noyori, Yu. Watanabe, H. Takechi, K. Matsumura, B. Långström, Y. Watanabe, Angew. Chem. 1996, 108, 366-369;
23. Angew. Chem. Int. Ed. Engl. 1996, 35, 334-336;
24. b) H. Takechi, K. Matsumura, Yu. Watanabe, K. Kato. R. Noyori, M. Suzuki, Y. Watanabe, J. Biol. Chem. 1996, 271, 5901-5906.
25. 11C]methyl iodide and an organoboron, see, a) Y. Andersson, A. Cheng. B. Långström. Acta Chem. Scand. 1995, 49, 683-688;
26. b) E. D. Hosteller. S. Fallis, T. J. McCarthy. M. J. Welch, J. A. Katze-nellenbogen, J. Org. Chem. 1998, 63, 1348-1351;
27. c) T. G. Hamill, S. Krause, C. Ryan, C. Bonnefous, S. Govek, T. J. Seiders, N. D. P. Cosford, J. Roppe, T. Kamenecka, S. Patel, R. E. Gibson, S. Sanabria, K. Riffel, W. Eng, C. King, X. Yang, M. D. Green, S. S. O'Malley, R. Hargreaves, H. D. Burns, Synapse 2005, 56, 205-216.
28. E. D. Hostetler, G. E. Terry, H. D. Burns, J. Labelled Compd. Radiopharm. 2005, 48, 629-634.
29. M. Suzuki, H. Doi, H. Tsukada, Method of rapid methylation, kit for preparing PET tracer and method of producing PET tracer, Pub. No. WO/2008/023780 (International Application No. PCT/JP2007/066411).
30. 11C]methylstannane under Pd catalysis have been reported - see: a) T. Forngren, L. Samuelsson, B. Långström, J. Labelled Compd. Radiopharm. 2004, 47, 71-78;
31. b) M. Huiban, A. Huet, L. Barré, F. Sobrio, E. Fouquet, C. Perrio, Chem. Commun. 2006, 97-99.
32. a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
33. b) A. Suzuki, J. Organomet Chem. 1999, 576, 147-168;
34. c) A. Suzuki in Modern Arene Chemistry (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002, pp. 53-106;
35. d) A. Suzuki, H. C Brown, Suzuki Coupling, Organic Syntheses via Boranes, Vol. 3. Aldrich Chemical, Milwaukee 2003;
36. e) A. Suzuki, Proc. Jpn. Acad. Ser. B 2004, 80, 359-371;
37. f) F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 2419-2440;
38. g) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695;
39. h) N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; for the cross-coupling reactions between alkyl iodide and boron compounds by the Suzuki-Miyaura reaction, see:
40. i) T. Ishiyama, S. Abe, N. Miyaura. A. Suzuki, Chem, Lett. 1992, 691-694;
41. j) L. J. Gooşen, Appl. Organomet. Chem. 2004, 18, 602-604.
42. a) C. A. Tolman, Chem. Rev. 1977, 77, 313-348;
43. b) O. Niyomura, M. Tokunaga, Y. Obora, T. Iwasawa, Y. Tsuji, Angew. Chem. 2003, 115, 1325-1327;
44. Angew. Chem. Int. Ed. 2003, 42, 1287-1289.
45. [2c-e]
46. 0 complex.
47. a) L. Zheng, M.S. Berridge, Appl. Radiat. Isot. 2000, 52, 55-61;
48. b) M-C. Lasne, C. Perrio, J. Rouden, L. Barré, D. Roeda, F. Dolle, C. Crouzel in Contrast Agents II (Ed.: W. Krause), Springer, Berlin/Heidelberg, 2002, pp. 201-258;
49. c) M.-R. Zhang, M. Ogawa, K. Furutsuka. Y. Yoshida, K. Suzuki, J. Fluorine Chem. 2004, 125, 1879-1886.
50. 11C]Celecoxib, see, J. Prabhakaran, V. J. Majo, N. R. Simpson, R. L. V. Heertum, J. J. Mann, J. S. D. Kumar, J. Labelled Compd. Radiopharm. 2005, 48, 887-895;
51. b) T. D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, L. F. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. D. Anderson, E. G. Burton, J. N. Cogburn, S. A. Gregory, C. M. Koboldt, W. E. Perkins, K. Seibert, A. W. Veenhuizen, Y. Y. Zhang, P. C. Isakson, J. Med. Chem. 1997, 40, 1347-1365.
52. 11C]-10 are in progress. Details will be reported separately.
53. a) F. G. Siméon, A. K. Brown, S. S. Zoghbi, V. M. Patterson, R. B. Innis, V. W. Pike, J. Med. Chem. 2007, 50, 3256-3266;
54. b) B. Halford, Chem. Eng. News 2008, 86, 13-20.
55. a) T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402;
56. b) S. R. Chemler, D. Trauner. S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701;
57. Angew. Chem. Int. Ed. 2001, 40, 4544-4568;
58. c) K. C. Nicolaou. P. G. Bulger. D. Sarlah, Angew. Chem. 2005, 117, 4516-4563;
59. Angew. Chem. Int. Ed. 2005, 44, 4442-4489.
60. I. J. Boyer, Toxicology 1989, 55, 253-298.
61. a) J. Takagi. K. Takahashi, T. Ishiyama, N. Miyaura, J. Am. Chem. Soc. 2002, 124, 8001-8006;
62. b) H. C. Brown, C. Subrahmanyam, T. Hamaoka, N. Ravindran, D. H. Bowman, S. Misumi, M. K. Unni, V. Somayaji, N. G. Bhat. J. Org. Chem. 1989, 54, 6068-6075.
63. D.X Burton, P. E. Greenlimb, J. Org. Chem. 1975, 40, 2796-2801; for Berridge's modified procedure, see reference [14a].