Scale-up of microwave-assisted reactions in a multimode bench-top reactor

Organic Process Research and Development

Volumn 15, Issue 4, 2011, Pages 841-854

  Dallinger, Doris ^a   Lehmann, Hansjörg ^b   Moseley, Jonathan D ^c   Stadler, Alexander ^d   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b NOVARTIS PHARMA AG   (Switzerland)

^c ASTRAZENECA   (United Kingdom)

^d ANTON PAAR GMBH   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC SUBSTITUTIONS; CROSS-COUPLINGS; DIELS-ALDER REACTION; DIFFERENT SOLVENTS; HETEROCYCLE SYNTHESIS; KNOEVENAGEL CONDENSATION; LABORATORY SCALE; MICROWAVE ABSORBING; MICROWAVE-ASSISTED; MICROWAVE-ASSISTED REACTIONS; MULTIMODES; OPTIMIZED REACTION CONDITIONS; ORGANIC REACTION; PRODUCT YIELDS; REACTION VESSEL; REACTION VOLUME; SCALE-UP; SINGLE-MODE MICROWAVES;

BATCH REACTORS; SYNTHESIS (CHEMICAL);

MICROWAVES;

EID: 79960519076     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200090k     Document Type: Article

References (127)

1. For a recent review with >900 references and a tabular survey of ∼200 microwave chemistry review articles, books, and book chapters, see: Kappe, C. O.; Dallinger, D. Mol. Diversity 2009, 13, 71-193
2. Caddick, S.; Fitzmaurice, R. Tetrahedron 2009, 65, 3325-3355 and references cited therein
3. Microwave Heating as a Tool for Sustainable Chemistry; Leadbeater, N. E., Ed.; CRC Press, Taylor & Francis Group: Boca Raton, USA, 2011.
4. Aqueous Microwave-Assisted Chemistry; Polshettiwar, V.; Varma, R. S., Eds.; Royal Society of Chemistry: Cambridge, U.K., 2010.
5. Microwave-Assisted Organic Synthesis; Lidström, P.; Tierney, J. P., Eds.; Blackwell Publishing: Oxford, U.K., 2005.
6. Microwaves in Organic Synthesis, 2 nd ed.; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
7. Microwave Methods in Organic Synthesis; Larhed, M.; Olofsson, K., Eds.; Springer: Berlin, Germany, 2006.
8. Kappe, C. O.; Dallinger, D.; Murphree, S. S. Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols; Wiley-VCH: Weinheim, 2009.
9. Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406-415
10. Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, Germany, 2005.
11. Kappe, C. O.; Dallinger, D. Nat. Rev. Drug Discovery 2006, 5, 51-63
12. Chighine, A.; Sechi, G.; Bradley, M. Drug Discovery Today 2007, 12, 459-464
13. Raner, K. D.; Strauss, C. R.; Trainor, R. W.; Thorn, J. S. J. Org. Chem. 1995, 60, 2456-2460 For reviews, see: Moseley, J. D. In Microwave Heating as a Tool for Sustainable Chemistry; Leadbeater, N. E., Ed.; CRC Press, Taylor & Francis Group: Boca Raton, 2011; pp 105-147.
14. Strauss, C. R. Org. Process Res. Dev. 2009, 13, 915-923
15. Lehmann, H. In New Avenues to Efficient Chemical Synthesis; Seeberger, P. H.; Blume, T., Eds.; Springer-Verlag: Berlin, 2007.
16. Kremsner, J. M.; Stadler, A.; Kappe, C. O. Top. Curr. Chem. 2006, 266, 233-278
17. Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S.; Mingos, D. M. P. Chem. Soc. Rev. 1998, 27, 213-224
18. Horikoshi, S.; Iida, S.; Kajitani, M.; Sato, S.; Serpone, N. Org. Process Res. Dev. 2008, 12, 257-263
19. For reviews on microwave-assisted continuous flow processing, see: Singh, B. K.; Kaval, N.; Tomar, S.; Van der Eycken, E.; Parmar, V. S. Org. Process Res. Dev. 2008, 12, 468-474
20. Baxendale, I. R.; Hayward, J. J.; Ley, S. V. Comb. Chem. High Throughput Screening 2007, 10, 802-836
21. Glasnov, T. N.; Kappe, C. O. Macromol. Rapid Commun. 2007, 28, 395-410
22. For selected recent examples, see: Ullah, F.; Samarakoon, T.; Rolfe, A.; Kurtz, R. D.; Hanson, P. R.; Organ, M. G. Chem.-Eur. J. 2010, 16, 10959-10962
23. Dressen, M. H. C. L.; Van de Kruijs, B. H. P.; Meduldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. Org. Process Res. Dev. 2010, 14, 351-361
24. Bergamelli, F.; Ianelli, M.; Marafie, J. A.; Moseley, J. D. Org. Process Res. Dev. 2010, 14, 926-930
25. Bagley, M. C.; Fusillo, V.; Jenkins, R. L.; Lubinu, M. C.; Mason, C. Org. Biomol. Chem. 2010, 8, 2245-2251
26. Moseley, J. D.; Lawton, S. J. Chem. Today 2007, 25 (2) 16-19
27. Benaskar, F.; Hessel, V.; Krtschil, Löb, P.; Stark, A. Org. Process Res. Dev. 2009, 13, 970-982
28. Dressen, M. H. C. L.; Van de Kruijs, B. H. P.; Meduldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. Org. Process Res. Dev. 2009, 13, 888-895
29. Leadbeater, N. E.; Barnard, T. M.; Stencel, L. M. Energy Fuels 2008, 22, 2005-2008
30. Smith, C. J.; Iglesias-Sigüenza, F. J.; Baxendale, I. R.; Ley, S. V. Org. Biomol. Chem. 2007, 5, 2758-2761
31. Shore, G.; Morin, S.; Mallik, D.; Organ, M. G. Chem.-Eur. J. 2008, 14, 1351-1356
32. Lehmann, H.; La Vecchia, L. Org. Process Res. Dev. 2010, 14, 650-656
33. Schmink, J. R.; Kormos, C. M.; Devine, W. G.; Leadbeater, N. E. Org. Process Res. Dev. 2010, 14, 205-214
34. Bowman, M. D.; Schmink, J. R.; McGowan, C. M.; Kormos, C. M.; Leadbeater, N. E. Org. Process. Res. Dev. 2008, 12, 1078-1088
35. Ianelli, M.; Bergamelli, F.; Kormos, C. M.; Paravisi, S.; Leadbeater, N. E. Org. Process Res. Dev. 2009, 13, 634-637
36. Bowman, M. D.; Holcomb, J. L.; Kormos, C. M.; Leadbeater, N. E.; Williams, V. A. Org. Process Res. Dev. 2008, 12, 41-57
37. Moseley, J. D.; Lenden, P.; Lockwood, M.; Ruda, K.; Sherlock, J.-P.; Thomson, A. D.; Gilday, J. P. Org. Process Res. Dev. 2008, 12, 30-40
38. Appukkuttan, P.; Axelsson, L.; Van der Eycken, E.; Larhed, M. Tetrahedron Lett. 2008, 49, 5625-5628
39. Pawluczyk, J. M.; McClain, R. T.; Denicola, C.; Mulhearn, J. J., Jr.; Rudd, D. J.; Lindsley, C. W. Tetrahedron Lett. 2007, 48, 1497-1501
40. Hoogenboom, R.; Paulus, R. M.; Pilotti, Å.; Schubert, U. S. Macromol. Rapid Commun. 2006, 27, 1556-1560
41. Carlsson, A.-C.; Jam, F.; Tullberg, M.; Pilotti, Å.; Ioannidis, P.; Luthman, K.; Grøtli, M. Tetrahedron Lett. 2006, 47, 5199-5201
42. Damm, M.; Glasnov, T. N.; Kappe, C. O. Org. Process. Res. Dev. 2010, 14, 215-224
43. Moseley, J. D.; Woodman, E. K. Energy Fuels 2009, 23, 5438-5447
44. Stadler, A.; Yousefi, B. H.; Dallinger, D.; Walla, P.; van der Eycken, E.; Kaval, N.; Kappe, C. O. Org. Process Res. Dev. 2003, 7, 707-716
45. Alcázar, J.; Diels, G.; Schoentjes, B. QSAR Comb. Sci. 2004, 23, 906-910
46. Loones, K. T. J.; Maes, B. U. W.; Rombouts, G.; Hostyn, S.; Diels, G. Tetrahedron 2008, 61, 10338-10348
47. For further details, see: www.anton-paar.com (accessed June 24, 2011).
48. For the importance of internal temperature measurement in microwave chemistry, see: Obermayer, D.; Kappe, C. O. Org. Biomol. Chem. 2010, 8, 114-121
49. Obermayer, D.; Gutmann, D.; Kappe, C. O. Angew. Chem., Int. Ed. 2009, 48, 8321-8324
50. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698
51. Pindur, U.; Lutz, G.; Otto, G. Chem. Rev. 1993, 93, 741-761
52. Godwin, D. R.; Lawton, S. J.; Moseley, J. D.; Welham, M. J.; Weston, N. P. Energy Fuels 2010, 24, 5446-5453
53. Razzaq, T.; Kappe, C. O. ChemSusChem 2008, 1, 123-132
54. Razzaq, T.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 6321-6329
55. Newman, M. S.; Karnes, H. A. J. Org. Chem. 1966, 31, 3980-3984
56. Kwart, H.; Evans, E. R. J. Org. Chem. 1966, 31, 410-412
57. For a recent review, see: Lloyd-Jones, G. C.; Moseley, J. D.; Renny, J. S. Synthesis 2008, 661-689
58. Gilday, J. P.; Lenden, P.; Moseley, J. D.; Cox, B. G. J. Org. Chem. 2008, 73, 3130-3134
59. Moseley, J. D.; Lenden, P. Tetrahedron 2007, 63, 4120-4125
60. Moseley, J. D.; Sankey, R. F.; Tang, O. N.; Gilday, J. P. Tetrahedron 2006, 62, 4685-4689
61. Herrero, M. A.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 36-47
62. Moseley, J. D.; Lenden, P.; Thomson, A. D.; Gilday, J. P. Tetrahedron Lett. 2007, 48, 6084-6087
63. Moseley, J. D.; Woodman, E. K. Org. Process Res. Dev. 2008, 12, 967-981
64. Bowden, S. A.; Burke, J. N.; Gray, F.; McKown, S.; Moseley, J. D.; Moss, W. O.; Murray, P. M.; Welham, M. J.; Young, M. J. Org. Process Res. Dev. 2004, 8, 33-44
65. Alamgir, M.; Black, D. St. C.; Kumar, N. Synthesis, Reactivity and Biological Activity of Benzimidazoles. In Bioactive Heterocycles III; Khan, M. T. H., Ed.; Topics in Heterocyclic Chemistry; Springer: Berlin, Germany, 2007; Vol. 9, pp 87-118 and references therein.
66. Dubey, R.; Moorthy, N. S. Chem. Pharm. Bull. 2007, 55, 115-117
67. Kumar, B. V. S.; Vaidya, S. D.; Kumar, R. V.; Bhirud, S. B.; Mane, R. B. Eur. J. Med. Chem. 2006, 41, 599-604
68. Martinez- Palou, R.; Zepeda, L. G.; Hoepfl, H.; Montoya, A.; Guzman-Lucero, D. J.; Guzman, J. Mol. Diversity 2005, 9, 361-369
69. Navarrete- Vazquez, G.; Moreno-Diaz, H.; Aguirre-Crespo, F.; Leon-Rivera, I.; Villalobos-Molina, R.; Munoz-Muniz, O.; Estrada-Soto, S. Bioorg. Med. Chem. Lett. 2006, 16, 4169-4173
70. Treu, M.; Karner, T.; Kousek, R.; Berger, H.; Mayer, M.; McConnell, D. B.; Stadler, A. J. Comb. Chem. 2008, 10, 863-868
71. Damm, M.; Kappe, C. O. Mol. Diversity 2009, 13, 529-543
72. Sinha, A. K.; Sharma, A.; Joshi, B. P. Tetrahedron 2007, 63, 960-965
73. Murphree, S. S.; Kappe, C. O. J. Chem. Educ. 2009, 86, 227-229
74. Bendich, A.; Russel, P.; Fox, J. J. Am. Chem. Soc. 1954, 76, 6073-6077
75. For an overview see: Hepworth, J. D.; Gabbut, C. D.; Heron, B. M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; McKillop, A., Eds.; Pergamon: Oxford, 1996; Vol. 5, Chapter 8.
76. Majumdar, K. C.; Mondal, S. Tetrahedron Lett. 2008, 49, 2418-2420
77. Yamamoto, Y.; Kirai, N. Org. Lett. 2008, 10, 5513-5516
78. Ajani, O. O.; Nwinyi, O. C. J. Heterocycl. Chem. 2010, 47, 179-187
79. Rong, L. C.; Li, X. Y.; Shi, D. Q.; Tu, S. J.; Zhuang, Q. Y. Synth. Commun. 2007, 37, 183-189
80. Rajitha, B.; Kumar, V. N.; Someshwar, P.; Madhav, J. V.; Reddy, P. N.; Reddy, Y. T. ARKIVOC 2006, 23-27
81. Al-Zaydi, K. M. Molecules 2003, 8, 541-555
82. Frere, S.; Thiery, V.; Besson, T. Tetrahedron Lett. 2001, 42, 2791-2794
83. de la Hoz, A.; Moreno, A.; Vazquez, E. Synlett 1999, 608-610
84. Bogdal, D. J. Chem. Res. 1998, 468-469
85. Schmink, J. R.; Holcomb, J. L.; Leadbeater, N. E. Chem.-Eur. J. 2008, 14, 9943-9950
86. Schmink, J. R.; Leadbeater, N. E. Nat. Protoc. 2008, 3, 1-7
87. Marafie, J. A.; Moseley, J. D. Org. Biomol. Chem. 2010, 8, 2219-2227
88. NAr reaction on small scale, see: Cherng, Y.-J. Tetrahedron 2002, 58, 4931-4935
89. Li, F.; Wang, Q.; Ding, Z.; Tao, F. Org. Lett. 2003, 5, 2169-2171
90. Rebeiro, G. L.; Khadilkar, B. M. Synth. Commun. 2003, 33, 1405-1410
91. F. Li, F.; Meng, Q.; Chen, H.; Li, Z.; Wang, Q.; Tao, F. Synthesis 2005, 1305-1313
92. Xu, H.; Chen, Y. Synth. Commun. 2007, 37, 2411-2420
93. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-VCH: Weinheim, 2002; Vol. 1, p 1133.
94. Dugger, R. W.; Ragan, J. A.; Ripin, D. H. B. Org. Process. Res. Dev. 2005, 9, 253-258
95. For reviews covering the topic, see: Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771-11835
96. Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727
97. For the first report, see: Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582-9584
98. Arvela, R. K.; Leadbeater, N. E. J. Org. Chem. 2005, 70, 1786-1790
99. Leadbeater, N. E.; Williams, V. A.; Barnard, T. M.; Collins, M. J., Jr. Synlett 2006, 18, 2953-2958
100. Arvela, R. K.; Leadbeater, N. E.; Collins, M. J., Jr. Tetrahedron 2005, 61, 9349-9355
101. For reviews, see: Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419-2440
102. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470
103. Kotha, S.; Lahiri, S.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695
104. For a review, see: Leadbeater, N. E. Chem. Commun. 2005, 2881-2902
105. Leadbeater, N. E.; Schmink, J. R. Tetrahedron 2007, 63, 6764-6773
106. Leadbeater, N. E.; Smith, R. J. Org. Biomol. Chem. 2007, 5, 2770-2774
107. Arvela, R. K.; Leadbeater, N. E.; Mack, T. M.; Kormos, C. M. Tetrahedron Lett. 2006, 47, 217-220
108. Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. S. J. Org. Chem. 2005, 70, 161-168
109. Arvela, R. K.; Leadbeater, N. E. Org. Lett. 2005, 7, 2101-2104
110. Leadbeater, N. E.; Williams, V. A.; Barnard, T. M.; Collins, M. J., Jr. Org. Process Res. Dev. 2006, 10, 883-837
111. Devine, W. G.; Leadbeater, N. E. ARKIVOC 2011, v) 127-143
112. Arvela, R. K.; Leadbeater, N. E.; Collins, M. J., Jr. Tetrahedron 2005, 61, 9349-9355
113. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360-413
114. For reviews on the Biginelli reaction, see: Kappe, C. O. Acc. Chem. Res. 2000, 33, 879-888
115. Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043-1052
116. Dallinger, D.; Kappe, C. O. Nat. Protoc. 2007, 2, 1713-1721
117. Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971-974
118. Prokopcová, H.; Dallinger, D.; Uray, G.; Kaan, H. Y. K.; Ulaganathan, V.; Kozielski, F.; Laggner, C.; Kappe, C. O. ChemMedChem 2010, 5, 1760-1769
119. Kaan, H. Y. K.; Ulaganathan, V.; Rath, O.; Prokopcová, H.; Dallinger, D.; Kappe, C. O.; Kozielski, F. J. Med. Chem. 2010, 53, 5676-5683
120. Kappe, C. O.; Stadler, A. Methods Enzymol. 2003, 369, 197-223
121. Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 41, 9075-9078
122. Zhu, Y.; Pan, Y.; Huang, S. Synth. Commun. 2004, 34, 3167-3174
123. Matloobi, M.; Kappe, C. O. J. Comb. Chem. 2007, 9, 275-284
124. Prokopcová, H.; Pisani, L.; Kappe, C. O. Synlett 2007, 43-46
125. Regan, J.; Breitfelder, S.; Cirillo, P. J. Med. Chem. 2002, 45, 2994-3008
126. For a previous example on the use of the Masterwave BTR for the scale-up of a Ni-catalyzed cross-coupling reaction, see: Baghbanzadeh, M.; Pilger, C.; Kappe, C. O. J. Org. Chem. 2011, 76, 1507-1510
127. For a critical analysis of heating and energy efficiency in microwave chemistry, see: Moseley, J. D.; Kappe, C. O. Green Chem. 2011, 13, 794-806