A versatile route to 3-(pyrimidin-4-yl)-imidazo[1,2-a]pyridines and 3-(pyrimidin-4-yl)-pyrazolo[1,5-a]pyridines

被引:13
作者
Ducray, Richard [1 ]
Boutron, Pascal [1 ]
Didelot, Myriam [1 ]
Germain, Herve [1 ]
Lach, Franck [1 ]
Lamorlette, Maryannick [1 ]
Legriffon, Antoine [1 ]
Maudet, Mickael [1 ]
Menard, Morgan [1 ]
Pasquet, Georges [1 ]
Renaud, Fabrice [1 ]
Simpson, Iain [2 ]
Young, Gail L. [2 ]
机构
[1] AstraZeneca, Res Ctr, ZI Pompelle, F-51689 Reims 2, France
[2] AstraZeneca, Canc Med Chem, Macclesfield SK10 4TG, Cheshire, England
关键词
IMIDAZOPYRIDINE ANTICOCCIDIAL AGENTS; DEPENDENT KINASE INHIBITORS; BIOLOGICAL-ACTIVITY; SELECTIVE CLASS; POTENT ACTIVITY; PART II; SAR; HERPESVIRUSES; OPTIMIZATION; DERIVATIVES;
D O I
10.1016/j.tetlet.2010.07.024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A two-step synthesis of 3-(2-chloropyrimidin-4-yl)imidazo[1,2-a]pyridines is presented. The late stage elaboration of the imidazopyridine through a cyclocondensation allows a rapid access to a variety of substitution patterns. The intermediate enol ethers were obtained from inexpensive reagents in a ligand-free Heck coupling. This methodology has been extended to the formation of pyrazolo[1,5-a]pyridines via a formal 1,3-dipolar cycloaddition. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4755 / 4758
页数:4
相关论文
共 21 条
  • [1] Synthesis and SAR of aminopyrimidines as novel c-Jun N-terminal kinase (JNK) inhibitors
    Alam, Mahbub
    Beevers, Rebekah E.
    Ceska, Tom
    Davenport, Richard J.
    Dickson, Karen M.
    Fortunato, Mara
    Gowers, Lewis
    Haughan, Alan F.
    James, Lynwen A.
    Jones, Mark W.
    Kinsella, Natasha
    Lowe, Christopher
    Meissner, Johannes W. G.
    Nicolas, Anne-Lise
    Perry, Benjamin G.
    Phillips, David J.
    Pitt, William R.
    Platt, Adam
    Ratcliffe, Andrew J.
    Sharpe, Andrew
    Tait, Laura J.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (12) : 3463 - 3467
  • [2] Imidazo[1,2-a]pyridines:: A potent and selective class of cyclin-dependent kinase inhibitors identified through structure-based hybridisation
    Anderson, M
    Beattie, JF
    Breault, GA
    Breed, J
    Byth, KF
    Culshaw, JD
    Ellston, RPA
    Green, S
    Minshull, CA
    Norman, RA
    Pauptit, RA
    Stanway, J
    Thomas, AP
    Jewsbury, PJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (18) : 3021 - 3026
  • [3] Synthesis and SAR studies of very potent imidazopyridine antiprotozoal agents
    Biftu, T
    Feng, D
    Fisher, M
    Liang, GB
    Qian, XX
    Scribner, A
    Dennis, R
    Lee, S
    Liberator, PA
    Brown, C
    Gurnett, A
    Leavitt, PS
    Thompson, D
    Mathew, J
    Misura, A
    Samaras, S
    Tamas, T
    Sina, JF
    McNulty, KA
    McKnight, CG
    Schmatz, DM
    Wyvratt, M
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (09) : 2479 - 2483
  • [4] IRAK-4 inhibitors.: Part II:: A structure-based assessment of imidazo[1,2-a]pyridine binding
    Buckley, George M.
    Ceska, Thomas A.
    Fraser, Joanne L.
    Gowers, Lewis
    Groom, Colin R.
    Higueruelo, Alicia Perez
    Jenkins, Kerry
    Mack, Stephen R.
    Morgan, Trevor
    Parry, David M.
    Pitt, William R.
    Rausch, Oliver
    Richard, Marianna D.
    Sabin, Verity
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (11) : 3291 - 3295
  • [5] Expedient parallel synthesis of 2-amino-4-heteroarylpyrimidines
    Bursavich, MG
    Lombardi, S
    Gilbert, AM
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4113 - 4116
  • [6] Imidazo[1,2-α]pyridines.: Part 2:: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors
    Byth, KF
    Culshaw, JD
    Green, S
    Oakes, SE
    Thomas, AP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) : 2245 - 2248
  • [7] Poly(ethylene glycol) (PEG) as a reusable solvent medium for organic synthesis. Application in the Heck reaction
    Chandrasekhar, S
    Narsihmulu, C
    Sultana, SS
    Reddy, NR
    [J]. ORGANIC LETTERS, 2002, 4 (25) : 4399 - 4401
  • [8] Efficient synthesis of novel dipyridoimidazoles and pyrido[1′,2′;1,2]imidazo[4,5-d]pyridazine derivatives
    Chezal, JM
    Moreau, E
    Chavignon, O
    Lartigue, C
    Blache, Y
    Teulade, JC
    [J]. TETRAHEDRON, 2003, 59 (31) : 5869 - 5878
  • [9] Selective terminal heck arylation of vinyl ethers with aryl chlorides: A combined experimental-computational approach including synthesis of betaxolol
    Datta, GK
    von Schenck, H
    Hallberg, A
    Larhed, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10) : 3896 - 3903
  • [10] Discovery and optimization of imidazo[1,2-α]pyridine inhibitors of insulin-like growth factor-1 receptor (IGF-1R)
    Emmitte, Kyle A.
    Wilson, Brian J.
    Baum, Erich W.
    Emerson, Holly K.
    Kuntz, Kevin W.
    Nailor, Kristen E.
    Salovich, James M.
    Smith, Stephon C.
    Cheung, Mui
    Gerding, Roseanne M.
    Stevens, Kirk L.
    Uehling, David E.
    Mook, Robert A., Jr.
    Moorthy, Ganesh S.
    Dickerson, Scott H.
    Hassell, Anne M.
    Leesnitzer, M. Anthony
    Shewchuk, Lisa M.
    Groy, Arthur
    Rowand, Jason L.
    Anderson, Kelly
    Atkins, Charity L.
    Yang, Jingsong
    Sabbatini, Peter
    Kumar, Rakesh
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (03) : 1004 - 1008