title: General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates.
abstract: A wide range of 2-pyridyl and other difficult-to-access heterocyclic N-methyliminodiacetic acid boronates can be readily prepared from the corresponding bromides via a new method involving direct transligation of 2-heterocyclic trialkoxyborate salts with N-methyliminodiacetic acid (MIDA) at elevated temperatures.
authors.affiliation: Howard Hughes Medical Institute, Roger Adams Lab, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
authors.forename: Graham R
authors.initials: GR
authors.lastname: Dick
authors.forename: David M
authors.initials: DM
authors.lastname: Knapp
authors.forename: Eric P
authors.initials: EP
authors.lastname: Gillis
authors.forename: Martin D
authors.initials: MD
authors.lastname: Burke
mesh_terms: D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007098:Imino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D006571:Heterocyclic Compounds; D007098:Imino Acids; C533766:N-methyliminodiacetic acid
references.citation: J Mol Graph Model. 2004 Sep;23(1):51-8
references.pmid: 15331053
references.citation: Angew Chem Int Ed Engl. 2004 Jan 3;43(3):366-9
references.pmid: 14705100
references.citation: J Am Chem Soc. 2008 Mar 19;130(11):3290-1
references.pmid: 18298122
references.citation: Org Lett. 2009 Jan 15;11(2):381-4
references.pmid: 19072215
references.citation: Curr Opin Drug Discov Devel. 2005 Nov;8(6):723-40
references.pmid: 16312148
references.citation: J Am Chem Soc. 2009 May 27;131(20):6961-3
references.pmid: 19405470
references.citation: Science. 1998 Oct 2;282(5386):63-8
references.pmid: 9756477
references.citation: Org Lett. 2009 Jan 15;11(2):345-7
references.pmid: 19093828
references.citation: J Org Chem. 2009 Feb 6;74(3):973-80
references.pmid: 19105735
references.citation: J Org Chem. 2004 Mar 19;69(6):2210-2
references.pmid: 15058977
references.citation: Chem Biol. 2000 Aug;7(8):593-9
references.pmid: 11048950
references.citation: Aldrichimica Acta. 2009;42(1):17-27
references.pmid: 22523433
references.citation: Bioorg Med Chem. 2008 Mar 15;16(6):2753-63
references.pmid: 18243712
references.citation: Bioorg Med Chem. 2009 Feb 1;17(3):1370-80
references.pmid: 19147366
references.citation: J Med Chem. 2007 Dec 27;50(26):6535-44
references.pmid: 18052117
references.citation: J Org Chem. 2006 May 12;71(10):3754-61
references.pmid: 16674046
references.citation: Acc Chem Res. 2007 Apr;40(4):275-86
references.pmid: 17256882
references.citation: Chem Rev. 2008 Jan;108(1):288-325
references.pmid: 18095714
references.citation: J Org Chem. 2002 Jul 12;67(14):4968-71
references.pmid: 12098315
references.citation: Science. 1972 Apr 21;176(4032):277-9
references.pmid: 5019779
references.citation: Angew Chem Int Ed Engl. 2008;47(25):4695-8
references.pmid: 18491343
references.citation: J Am Chem Soc. 2008 Oct 29;130(43):14084-5
references.pmid: 18837550
references.citation: Nucleic Acids Res. 2009 Aug;37(14):4757-63
references.pmid: 19515938
references.citation: J Org Chem. 2003 May 30;68(11):4302-14
references.pmid: 12762730
references.citation: Org Lett. 2006 Aug 31;8(18):4071-4
references.pmid: 16928076
references.citation: J Am Chem Soc. 2007 May 30;129(21):6716-7
references.pmid: 17488084
references.citation: Bioorg Med Chem Lett. 2009 Sep 15;19(18):5321-4
references.pmid: 19692239
references.citation: J Med Chem. 2009 Jan 8;52(1):33-47
references.pmid: 19072055
references.citation: J Org Chem. 2002 Jan 11;67(1):3-15
references.pmid: 11777432
references.citation: J Org Chem. 2008 Feb 15;73(4):1440-55
references.pmid: 18205384
references.citation: Angew Chem Int Ed Engl. 2008;47(5):928-31
references.pmid: 18081121
references.citation: Org Lett. 2006 Feb 16;8(4):793-5
references.pmid: 16468769
references.citation: J Am Chem Soc. 2008 Jan 16;130(2):466-8
references.pmid: 18081295
references.citation: Org Lett. 2000 Dec 28;2(26):4201-4
references.pmid: 11150199
references.citation: J Am Chem Soc. 2009 Mar 4;131(8):3104-18
references.pmid: 19199785
references.citation: J Med Chem. 2009 Apr 23;52(8):2571-86
references.pmid: 19323562
references.citation: J Am Chem Soc. 2009 Mar 4;131(8):3016-23
references.pmid: 19199620
references.citation: Bioorg Med Chem. 2003 Oct 15;11(21):4569-75
references.pmid: 14527553
references.citation: Science. 2004 Mar 19;303(5665):1805-10
references.pmid: 15031493