Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(16): 2651-2663
DOI: 10.1055/s-0030-1260110
DOI: 10.1055/s-0030-1260110
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Direct Access to 3-Aminoindazoles by Buchwald-Hartwig C-N Coupling Reaction
Further Information
Received
21 April 2011
Publication Date:
21 July 2011 (online)
Publication History
Publication Date:
21 July 2011 (online)
Abstract
An efficient synthesis of various N-substituted 3-aminoindazoles using Buchwald-Hartwig C-N coupling reaction is described. Several parameters were varied, including the nature of the halogen atom and the protecting group of the starting materials, as well as the effects of the catalyst system, base, solvent, and reaction time. The efficiency of microwave versus conventional heating was also compared to test the outcome of the reaction. Thus, by applying this recent knowledge about metal-catalyzed aminations, an alternative for the direct synthesis of primary 3-aminoindazoles has been provided.
Key words
indazoles - amination - cross-coupling - palladium - copper - microwave promoted amination
- 1
Crestey F.Stiebing S.Legay R.Collot V.Rault S. Tetrahedron 2007, 63: 419 -
2a
Crestey F.Collot V.Stiebing S.Rault S. Synthesis 2006, 3506 -
2b
Crestey F.Collot V.Stiebing S.Rault S. Tetrahedron 2006, 62: 7772 -
2c
Crestey F.Collot V.Stiebing S.Lohier J.-F.Sopkova-de Oliveira Santos J.Rault S. Tetrahedron Lett. 2007, 48: 2457 -
3a
Stocks MJ.Barber S.Ford R.Leroux F.St-Gallay S.Teague S.Xue Y. Bioorg. Med. Chem. Lett. 2005, 15: 3459 -
3b
Dai Y.Hartandi K.Ji Z.Ahmed AA.Albert DH.Bauch JL.Bouska JJ.Bousquet PF.Cunha GA.Glaser KB.Harris CM.Hickman D.Guo J.Li J.Marcotte PA.Marsh KC.Moskey MD.Martin RL.Olson AM.Osterling DJ.Pease LJ.Soni NB.Stewart KD.Stoll VS.Tapang P.Reuter DR.Davidsen SK.Michaelides MR. J. Med. Chem. 2007, 50: 1584 -
3c
Lee J.Choi H.Kim K.-H.Jeong S.Park J.-W.Baek C.-S.Lee S.-H. Bioorg. Med. Chem. Lett. 2008, 18: 2292 -
3d
Raffa D.Maggio B.Cascioferro S.Raimondi MV.Schillaci D.Gallo G.Daidone G.Plescia S.Meneghetti F.Bombieri G.Di Cristina A.Pipitone RM.Grimaudo S.Tolomeo M. Eur. J. Med. Chem. 2009, 44: 165 -
3e
Antonysamy S.Hirst G.Park F.Sprengeler P.Stappenbeck F.Steensma R.Wilson M.Wong M. Bioorg. Med. Chem. Lett. 2009, 19: 279 - 4
Kaltenbach RF.Patel M.Waltermire RE.Harris GD.Stone BRP.Klabe RM.Garber S.Bacheler LT.Cordova BC.Logue K.Wright MR.Erickson-Viitanen S.Trainor GL. Bioorg. Med. Chem. Lett. 2003, 13: 605 - 5
Vasudevan A.Souers AJ.Freeman JC.Verzal MK.Gao J.Mulhern MM.Wodka D.Lynch JK.Engstrom KM.Wagaw SH.Broddjian S.Dayton B.Falls DH.Bush E.Brune M.Shapiro RD.Marsh KC.Hernandez LE.Collins CA.Kym PR. Bioorg. Med. Chem. Lett. 2005, 15: 5293 - 6
Clutterbuck LA.Posada CG.Visintin C.Riddall DR.Lancaster B.Gane PJ.Garthwaite J.Selwood DL. J. Med. Chem. 2009, 52: 2694 -
7a
Moore PK.Wallace P.Gaffen Z.Hart SL.Babbedge RC. Br. J. Pharmacol. 1993, 110: 219 -
7b
Babbedge RC.Bland-Ward PA.Hart SL.Moore PK. Br. J. Pharmacol. 1993, 110: 225 -
7c
Elguero J.Alkorta I.Claramunt RM.Lopez C.Sanz D.Santa María D. Bioorg. Med. Chem. 2009, 17: 8027 -
7d
Manzanedo C.Aguilar MA.Ribeiro Do Coutob B.Rodríguez-Arias M.Minarro J. Neurosci. Lett. 2009, 464: 67 - 8
Boulouard M.Schumann-Bard P.Butt-Gueulle S.Lohou E.Stiebing S.Collot V.Rault S. Bioorg. Med. Chem. Lett. 2007, 17: 3177 -
9a
Sanger GJ.Nelson DR. Eur. J. Pharmacol. 1989, 159: 113 -
9b
Joshi PR.Suryanarayanan A.Hazai E.Schulte MK.Maksay G.Bikadi Z. Biochemistry 2006, 45: 1099 -
9c
Abdelsayed GG. Exp. Hematol. 2007, 35: 34 -
9d
Tuca A. Cancer Management Res. 2010, 2: 1 -
10a
Kharitonov VG.Sharma VS.Magde D.Koesling D. Biochemistry 1999, 38: 10699 -
10b
Collot V.Dallemagne P.Bovy PR.Rault S. Tetrahedron 1999, 55: 6917 -
10c
Bredt SD. Mol. Pharm. 2003, 63: 1206 -
10d
Hering KW.Artz JD.Pearson WH.Marletta MA. Bioorg. Med. Chem. Lett. 2006, 16: 618 -
10e
Wu SY.Pan SL.Chen TH.Liao CH.Huang DY.Guh JH.Chang YL.Kuo SC.Lee FY.Teng CM. Br. J. Pharmacol. 2008, 155: 505 -
10f
Keswani AN.Peyton KJ.Durante W.Schafer AI.Tulis DA. J. Cardiovasc. Pharmacol. Ther. 2009, 14: 116 - 11
Giorgioni G.Ruggieri S.Di Stefano A.Sozio P.Cinque B.Di Marzio L.Santoni G.Claudi F. Bioorg. Med. Chem. Lett. 2008, 18: 2445 -
12a
Collot V.Bovy PR.Rault S. Tetrahedron Lett. 2000, 41: 9053 -
12b
Crestey F.Lohou E.Stiebing S.Collot V.Rault S. Synlett 2009, 615 -
13a
Collot V.Varlet D.Rault S. Tetrahedron Lett. 2000, 41: 4363 -
14a
Arnautu A.Collot V.Calvo Ros J.Alayrac C.Witulski B.Rault S. Tetrahedron Lett. 2002, 43: 2695 -
14b
Witulski B.Azcon JR.Alayrac C.Arnautu A.Collot V.Rault S. Synthesis 2005, 771 - 15
Bouchet P.Lazaro R.Benchidmi M.Elguero J. Tetrahedron 1980, 36: 3523 - 16
Burke MJ.Trantow BM. Tetrahedron Lett. 2008, 49: 4579 -
17a
Kaltenbach RF.Klabe RM.Cordova BC.Seitz SP. Bioorg. Med. Chem. Lett. 1999, 9: 2259 -
17b
Lukin K.Hsu MC.Fernando D.Leanna MR. J. Org. Chem. 2006, 71: 8166 -
17c
Orsini P.Menichincheri M.Vanotti E.Panzeri A. Tetrahedron Lett. 2009, 50: 3098 - 18
Kruger AW.Rozema MJ.Chu-Kung A.Gandarilla J.Haight AR.Kotecki BJ.Richter SM.Schwartz AM.Wang Z. Org. Process Res. Dev. 2009, 13: 1419 - 19
Candiani I.D’Arasmo G.Heidempergher F.Tomasi A. Org. Process Res. Dev. 2009, 13: 456 -
20a
Leroy V.Lee GE.Lin J.Herman SH.Lee TB. Org. Process Res. Dev. 2001, 5: 179 -
20b
Watson TJ.Ayers TA.Shah N.Wenstrup D.Webster M.Freund D.Horgan S.Carey JP. Org. Process Res. Dev. 2003, 7: 521 - For Buchwald-Hartwig C-N coupling, see:
-
21a
Hartwig JF. Angew. Chem., Int. Ed. Engl. 1998, 37: 2046 -
21b
Yang B.Buchwald SL. J. Organomet. Chem. 1999, 576: 125 -
21c
Wolfe JP.Buchwald SL. J. Org. Chem. 2000, 65: 1144 -
21d
Wolfe JP.Tomori H.Sadighi JP.Yin J.Buchwald SL. J. Org. Chem. 2000, 65: 1158 -
21e
Ali MH.Buchwald SL. J. Org. Chem. 2001, 66: 2560 -
21f
Muci AR.Buchwald SL. Top. Curr. Chem. 2002, 219: 131 -
21g
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 -
21h
Martin R.Rivero MR.Buchwald SL. Angew. Chem. Int. Ed. 2006, 45: 7079 -
21i
Kienle M.Dubbaka SR.Brade K.Knochel P. Eur. J. Org. Chem. 2007, 4166 -
21j
Fors BP.Watson DA.Biscoe MR.Buchwald SL. J. Am. Chem. Soc. 2008, 130: 13552 -
21k
Surry DS.Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 6338 -
21l
Hartwig JF. Acc. Chem. Res. 2008, 41: 1534 -
21m
Fors BP.Davis NR.Buchwald SL. J. Am. Chem. Soc. 2009, 131: 5766 -
22a
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 -
22b
Evano G.Blanchard N.Toumi M. Chem. Rev. 2008, 108: 3054 -
22c
Monnier F.Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 6954 - For a few examples of applications of metal-catalyzed amination to heterocyclic compounds, see:
-
23a
Wagaw S.Buchwald SL. J. Org. Chem. 1996, 61: 7240 -
23b
Nishiyama M.Yamamoto T.Koie Y. Tetrahedron Lett. 1998, 39: 617 -
23c
Hooper MW.Utsunomiya M.Hartwig JF. J. Org. Chem. 2003, 68: 2861 -
23d
Enguehard C.Allouchi H.Gueiffier A.Buchwald SL. J. Org. Chem. 2003, 68: 4367 -
23e
Enguehard C.Allouchi H.Gueiffier A.Buchwald SL. J. Org. Chem. 2003, 68: 5614 -
23f
Ferreira ICFR.Queiroz M.-JRP.Kirsch G. Tetrahedron 2003, 59: 975 -
23g
Enguehard-Gueiffier C.Thery I.Gueiffier A.Buchwald SL. Tetrahedron 2006, 62: 6042 -
23h
Peng Z.-H.Journet M.Humphrey G. Org. Lett. 2006, 8: 395 -
23i
Calhelha RC.Queiroz M.-JRP. Tetrahedron Lett. 2010, 51: 281 -
23j
Das AR.Medda A.Singha R. Tetrahedron Lett. 2010, 51: 1099 -
24a
Santhakumar V, andTomaszewski M. inventors; Patent WO 2006/0052190. ; Chem. Abstr. 2006, 144, 488650 -
24b
Hisanori I,Takeshi I, andYoshimasa M. inventors; US Patent 2008/0036373. ; Chem. Abstr. 2008, 148, 272551 -
25a
Cooper AB, andDeng Y. inventors; US Patent 2009/0118284. ; Chem. Abstr. 2009, 150, 515160 -
26a
Bartsch RA.Yang IW. J. Heterocycl. Chem. 1984, 21: 1063 -
26b
Schumann P.Collot V.Hommet Y.Gsell W.Dauphin F.Sopkova J.MacKenzie E.Duval D.Boulouard M.Rault S. Bioorg. Med. Chem. Lett. 2001, 11: 1153 -
27a
Bocchi V.Palla G. Synthesis 1982, 1096 -
28a
Robins RK.Godefroi EF.Taylor EC.Lewis LR.Jackson A. J. Am. Chem. Soc. 1961, 83: 2574 -
28b
Sun J.-H.Teleha CA.Yan J.-S.Rodgers JD.Nugiel DA. J. Org. Chem. 1997, 62: 5627 -
29a
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250 -
30a
Maes BUW.Loones KTJ.Hostyn S.Dielsb G.Rombouts G. Tetrahedron 2004, 60: 11559 -
30b
Heo J.-N.Song YS.Kim BT. Tetrahedron Lett. 2005, 46: 4621 - 31
Jiang L.Lu X.Zhang H.Jiang Y.Ma D. J. Org. Chem. 2009, 74: 4542 - 32
Yeh VSC.Wiedeman PE. Tetrahedron Lett. 2006, 47: 6011 - 33
Kranenburg M.van der Burgt YEM.Kamer PCJ.van Leeuwen PWNM. Organometallics 1995, 14: 3081 -
34a
Yin J.Buchwald SL. Org. Lett. 2000, 2: 1101 -
34b
Queiroz M.-JRP.Calhelhaa RC.Kirsch G. Tetrahedron 2007, 63: 13000 -
34c
Audisio D.Messaoudi S.Peyrat J.-F.Brion J.-D.Alami M. Tetrahedron Lett. 2007, 48: 6928 -
35a
Röder JC.Meyer F.Pritzkow H. Organometallics 2001, 20: 811 -
35b
Röder JC.Meyer F.Winter RF.Kaifer E. J. Organomet. Chem. 2002, 641: 113 -
35c
Gérard A.-L.Bouillon A.Mahatsekake C.Collot V.Rault S. Tetrahedron Lett. 2006, 47: 4665 - 36
Lefebvre V.Cailly T.Fabis F.Rault S. J. Org. Chem. 2010, 75: 2730 -
37a
Wolfe JP.Ahman J.Sadighi JP.Singer RA.Buchwald SL. Tetrahedron Lett. 1997, 38: 6367 -
37b
Singer RA.Buchwald SL. Tetrahedron Lett. 1999, 40: 1095 -
37c
Grasa GA.Viciu MS.Huang J.Nolan SP. J. Org. Chem. 2001, 66: 7729 -
37d
Bhagwanth S.Adjabeng GM.Hornberger KR. Tetrahedron Lett. 2009, 50: 1582