{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T04:13:56Z","timestamp":1791432836678,"version":"4.3.3"},"reference-count":57,"publisher":"American Chemical Society (ACS)","issue":"7","funder":[{"DOI":"10.13039\/501100001655","name":"Deutscher Akademischer Austauschdienst","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001655","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000082","name":"Division of Graduate Education","doi-asserted-by":"publisher","award":["DGE-1346837"],"award-info":[{"award-number":["DGE-1346837"]}],"id":[{"id":"10.13039\/100000082","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100004319","name":"Pfizer","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100004319","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["1R35GM125052"],"award-info":[{"award-number":["1R35GM125052"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100011769","name":"Scripps Research Institute","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100011769","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2018,4,6]]},"DOI":"10.1021\/acs.joc.7b03100","type":"journal-article","created":{"date-parts":[[2018,3,2]],"date-time":"2018-03-02T16:12:56Z","timestamp":1520007176000},"page":"3417-3425","source":"Crossref","is-referenced-by-count":38,"title":["Copper-Catalyzed Chan\u2013Lam Cyclopropylation of Phenols and Azaheterocycles"],"prefix":"10.1021","volume":"83","author":[{"given":"Joseph","family":"Derosa","sequence":"first","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miriam L.","family":"O\u2019Duill","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthew","family":"Holcomb","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mark N.","family":"Boulous","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryan L.","family":"Patman","sequence":"additional","affiliation":[{"name":"Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fen","family":"Wang","sequence":"additional","affiliation":[{"name":"Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michelle","family":"Tran-Dub\u00e9","sequence":"additional","affiliation":[{"name":"Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Indrawan","family":"McAlpine","sequence":"additional","affiliation":[{"name":"Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2767-6556","authenticated-orcid":true,"given":"Keary M.","family":"Engle","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2018,3,2]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.6b00472"},{"key":"ref2\/cit2","doi-asserted-by":"publisher","DOI":"10.1021\/ed1003806"},{"key":"ref3\/cit3a","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2445"},{"key":"ref3\/cit3b","first-page":"381","volume":"45","author":"Edwards M. P.","year":"2010","journal-title":"Annu. Rep. Med. Chem."},{"key":"ref3\/cit3c","doi-asserted-by":"publisher","DOI":"10.4155\/fmc.12.208"},{"key":"ref3\/cit3d","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrestox.6b00043"},{"key":"ref4\/cit4","doi-asserted-by":"publisher","DOI":"10.1021\/ja065348u"},{"key":"ref5\/cit5","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2011.05.003"},{"key":"ref6\/cit6","doi-asserted-by":"publisher","DOI":"10.1021\/jm4008642"},{"key":"ref7\/cit7","doi-asserted-by":"publisher","DOI":"10.1021\/tx200168d"},{"key":"ref8\/cit8a","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b01641"},{"key":"ref8\/cit8b","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1380521"},{"key":"ref8\/cit8c","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b05215"},{"key":"ref8\/cit8d","doi-asserted-by":"publisher","DOI":"10.1021\/op500031z"},{"key":"ref8\/cit8e","doi-asserted-by":"publisher","DOI":"10.1021\/ol401004r"},{"key":"ref8\/cit8f","doi-asserted-by":"publisher","DOI":"10.1039\/b925499d"},{"key":"ref8\/cit8g","doi-asserted-by":"publisher","DOI":"10.1021\/ol800376f"},{"key":"ref8\/cit8h","doi-asserted-by":"publisher","DOI":"10.1021\/ja0676758"},{"key":"ref9\/cit9a","doi-asserted-by":"publisher","DOI":"10.1021\/jm1010644"},{"key":"ref9\/cit9b","doi-asserted-by":"publisher","DOI":"10.1021\/jm501350y"},{"key":"ref9\/cit9c","unstructured":"c Chen, S.; Bohnert, G.; Jiang, J.; Xia, Z. (Synta Pharmaceuticals Corporation) Compounds for Inflammation and Immune-Related Uses. World Patent WO2012151355 A1, Aug 11, 2012."},{"key":"ref9\/cit9d","doi-asserted-by":"publisher","DOI":"10.1124\/dmd.30.8.937"},{"key":"ref9\/cit9e","unstructured":"e Pelcman, B.; Olofsson, K.; Katkevics, M.; Ozola, V.; Suna, E.; Kalvins, I.; Trapencieris, P. (Biolipox AB) Indoles Useful in the Treatment of Inflammation. World Patent WO2006077364 A1, Jul 27, 2006."},{"key":"ref9\/cit9f","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.6b01928"},{"key":"ref10\/cit10a","doi-asserted-by":"publisher","DOI":"10.1021\/ja01249a507"},{"key":"ref10\/cit10b","doi-asserted-by":"publisher","DOI":"10.1021\/ja01151a053"},{"key":"ref11\/cit11a","first-page":"5","volume-title":"Organic Reactions","volume":"58","author":"Charette A. B.","year":"2001"},{"key":"ref11\/cit11b","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.02.004"},{"key":"ref12\/cit12a","unstructured":"a Takanobu, K.; Hiroki, S.; Hideyuki, I.; Minoru, S.; Kouhei, A.; Tsuyoshi, M. (Takeda Pharmaceutical Company Limited) Heteromonocyclic Compound and Use Thereof. World Patent WO2008062905 A2, May 29, 2008."},{"key":"ref12\/cit12b","unstructured":"b Barr, K. J.; Beinstock, C.; Maclean, J.; Zhang, H.; Beresis, R. T.; Zhang, D. (Merck, Sharp, and Dohme) 4-Heteroaryl Substituted Benzoic Acid Compounds as Rorgammat Inhibitors and Uses Therof. World Patent WO2014026327 A1, Feb 20, 2014."},{"key":"ref13\/cit13","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)00235-X"},{"key":"ref14\/cit14a","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00503-6"},{"key":"ref14\/cit14b","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00504-8"},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19842593"},{"key":"ref16\/cit16a","doi-asserted-by":"publisher","DOI":"10.1021\/ol034454n"},{"key":"ref16\/cit16b","doi-asserted-by":"publisher","DOI":"10.1021\/ol400323z"},{"key":"ref16\/cit16c","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b01077"},{"key":"ref17\/cit17a","doi-asserted-by":"publisher","DOI":"10.1021\/ol802882k"},{"key":"ref17\/cit17b","doi-asserted-by":"publisher","DOI":"10.1055\/s-0030-1258523"},{"key":"ref17\/cit17c","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.11.144"},{"key":"ref18\/cit18a","doi-asserted-by":"publisher","DOI":"10.1021\/ja9006657"},{"key":"ref18\/cit18b","doi-asserted-by":"publisher","DOI":"10.1021\/om300586p"},{"key":"ref18\/cit18c","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b12800"},{"key":"ref19\/cit19","unstructured":"Cacatian, S.; Claremon, D. A.; Dillad, L. W.; Fuchs, K.; Heine, N.; Jia, L.; Leftheris, K.; McKeever, B.; Morales-Ramos, A.; Singh, S.; Venkatamaran, S.; Wu, G.; Xu, Z.; Yuan, J.; Zhang, Y. (Vitae Pharmaceuticals, Boehringer Ingelheim) Inhibitors of Beta-Secretase. World Patent WO2010105179 A3, Nov 11, 2010."},{"key":"ref20\/cit20","first-page":"811","volume":"12","author":"Molander G. A.","year":"2009","journal-title":"Curr. Opin. Drug Discovery Devel"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60197H"},{"key":"ref22\/cit22a","doi-asserted-by":"publisher","DOI":"10.1039\/c0gc00106f"},{"key":"ref24\/cit24a","doi-asserted-by":"publisher","DOI":"10.1080\/00397911.2010.539758"},{"key":"ref24\/cit24b","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc42575d"},{"key":"ref24\/cit24c","unstructured":"c Liu, C.; Lin, J.; Moslin, R. M.; Weinstein, D. S.; Tokarski, J. S. (Bristol-Myers Squibb Company) Imidazopyridazine compounds useful as modulators of IL-12, IL-23 and\/or IFN alpha responses. World Patent WO2015089143 A1, Jun 18, 2015."},{"key":"ref24\/cit24d","unstructured":"d Martin, L.; Steurer, S.; Cockcroft, X.L. (Boehringer Ingleheim International) New pyridinones and isoquinolinones as inhibitors of the bromodomain brd9. World Patent WO2016139361 A1, Sep 9, 2016."},{"key":"ref25\/cit25","unstructured":"Menet, C. J. M.; Schmitt, B. A.; Geney, R. J. J.; Doyle, K. J.; Peach, J.; Palmer, N. J.; Jones, G. P.; Hardy, D.; Duffy, J.\nE. S. (Galapagos NV) Imidazo[4,5-C]pyridine Derivatives Useful for the Treatment of Degenerative and Inflammatory Diseases. World Patent WO 2013117645 A1, Aug 15, 2013."},{"key":"ref26\/cit26","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02650"},{"key":"ref27\/cit27","doi-asserted-by":"publisher","DOI":"10.1021\/ja011981y"},{"key":"ref28\/cit28","doi-asserted-by":"publisher","DOI":"10.1021\/ja1112518"},{"key":"ref29\/cit29","unstructured":"CCDC\n1584673 (\n                      8a\u2032\n                      ) contains the supplementary crystallographic\ndata for this paper. These data can be obtained free of charge from\nThe Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"ref30\/cit30","unstructured":"Bai, H.; Bailey, S.; Bhumralkar, D. R.; Bi, F.; Guo, F.; He, M.; Humphries, P. S.; Ling, A. L.; Luo, J.; Nukui, S.; Zhou, R. (Pfizer, Inc.) Fused Phenyl Amido Heterocyclic Compounds for the Prevention and Treatment of Glucokinase-Mediated Diseases World Patent WO2007122482 A1, Nov 1, 2007."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.7b03100","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,17]],"date-time":"2023-04-17T08:52:34Z","timestamp":1681721554000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.7b03100"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,3,2]]},"references-count":57,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2018,4,6]]}},"alternative-id":["10.1021\/acs.joc.7b03100"],"URL":"https:\/\/doi.org\/10.1021\/acs.joc.7b03100","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,3,2]]}}}