Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C–H/N–H Coupling

Lanfei Zhang; Xiaofei Zhang; Yongmei Cui; Chunhao Yang

doi:10.1055/a-1509-8624

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(20): 3815-3826
DOI: 10.1055/a-1509-8624

paper

Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C–H/N–H Coupling

Authors

Lanfei Zhang

^aDepartment of Chemistry, Shanghai University, 99 Shang Da Road, Shanghai 200444, P. R. of China

^bState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, 555 Zu Chong Zhi Road, Shanghai 201203, P. R. of China
Xiaofei Zhang

^bState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, 555 Zu Chong Zhi Road, Shanghai 201203, P. R. of China
Yongmei Cui∗

^aDepartment of Chemistry, Shanghai University, 99 Shang Da Road, Shanghai 200444, P. R. of China
Chunhao Yang ∗

^bState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, 555 Zu Chong Zhi Road, Shanghai 201203, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Abstract

Herein, a direct method for the synthesis of 3-fluoroindoles and 3,3-difluoroindolines from easily accessible 2,2-difluoro-2-phenylethan-1-amines is presented. This protocol was performed by Pd-catalyzed direct C–H/N–H coupling and employed picolinamide as a directing group. By controlling the temperature for this transformation, various 3,3-difluoroindolines and 3-fluoroindoles could be isolated with moderate to good yields.

Key words

picolinamide - 3,3-difluoroindolines - 3-fluoroindoles - directing groups

Volltext

Referenzen

References

1a Qin M, Cao Q, Wu X, Liu C, Zheng S, Xie H, Tian Y, Xie J, Zhao Y, Hou Y, Zhang X, Xu B, Zhang H, Wang X. Eur. J. Med. Chem. 2020; 186: 111856
1b Wang S.-Y, Shi X.-C, Laborda P. Eur. J. Med. Chem. 2020; 185: 111847
1c Zhu Y, Sun N, Yu M, Guo H, Xie Q, Wang Y. Eur. J. Org. Chem. 2019; 111589
1d Melander RJ, Minvielle MJ, Melander C. Tetrahedron 2014; 70: 6363
1e Sibel S. Curr. Org. Chem. 2017; 21: 2068
1f Zeeli S, Weill T, Finkin-Groner E, Bejar C, Melamed M, Furman S, Zhenin M, Nudelman A, Weinstock M. J. Med. Chem. 2018; 61: 4004

2 Teena S, Sanjiv K, Balasubramanian N. Cent. Nerv. Syst. Agents Med. Chem. 2016; 16: 19
3 Namasivayam V, Vanangamudi M, Kramer VG, Kurup S, Zhan P, Liu X, Kongsted J, Byrareddy SN. J. Med. Chem. 2019; 62: 4851
4 Drayson P, Mahdi A, Tarassenko L, Watkinson P. WO2019211632A1, 2019

5a Yu Y, Zhong J.-S, Xu K, Yuan Y, Ye K.-Y. Adv. Synth. Catal. 2020; 362: 2102
5b Neto JS. S, Zeni G. Org. Chem. Front. 2020; 7: 155
5c Nagaraju K, Ma D. Chem. Soc. Rev. 2018; 47: 8018
5d Mondal D, Kalar PL, Kori S, Gayen S, Das K. Curr. Org. Chem. 2020; 24: 2665
5e Colella M, Degennaro L, Luisi R. Molecules 2020; 25: 3242
5f Christodoulou MS, Beccalli EM, Foschi F, Giofre S. Synthesis 2020; 52: 2731
5g Aggarwal T, Sushmita, Verma AK. Org. Biomol. Chem. 2019; 17: 8330

6 Wang J, Sanchez-Rosello M, Acena JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432
7 Zimmer LE, Sparr C, Gilmour R. Angew. Chem. Int. Ed. 2011; 50: 11860
8 Nazaré M, Will DW, Matter H, Schreuder H, Ritter K, Urmann M, Essrich M, Bauer A, Wagner M, Czech J, Lorenz M, Laux V, Wehner V. J. Med. Chem. 2005; 48: 4511
9 Young BL, Cooks RG, Madden MC, Bair M, Jia J, Aubry A.-F, Miller SA. J. Pharm. Biomed. Anal. 2007; 43: 1602
10 Ma C, Gao P, Chu J, Wu X, Wen C, Kang D, Bai J, Pei X. WO2017211303A1, 2017

11a Zhang B, Zhang X, Hao J, Yang C. Org. Lett. 2017; 19: 1780
11b Zeidan N, Zambri M, Unger S, Dank C, Torelli A, Mirabi B, Lautens M. Org. Lett. 2020; 22: 3688
11c Fujita T, Sugiyama K, Sanada S, Ichitsuka T, Ichikawa J. Org. Lett. 2016; 18: 248
11d Nosova EV, Lipunova GN, Charushin VN, Chupakhin ON. J. Fluorine Chem. 2018; 212: 51
11e Fujita T, Watabe Y, Yamashita S, Tanabe H, Nojima T, Ichikawa J. Chem. Lett. 2016; 45: 964

12a Torres J, Garden SJ, Pinto AC, da Silva FS. Q, Boechat N. Tetrahedron 1999; 55: 1881
12b Arcadi A, Pietropaolo E, Alvino A, Michelet V. Org. Lett. 2013; 15: 2766
12c Yang L, Ma Y, Song F, You J. Chem. Commun. 2014; 50: 3024
12d Jiang X, Zhang F, Yang J, Yu P, Yi P, Sun Y, Wang Y. Adv. Synth. Catal. 2017; 359: 853
12e Yuan X, Yao JF, Tang ZY. Org. Lett. 2017; 19: 1410
12f Panferova LI, Smirnov VO, Levin VV, Kokorekin VA, Struchkova MI, Dilman AD. J. Org. Chem. 2017; 82: 745
12g Bora PP, Bihani M, Plummer S, Gallou F, Handa S. ChemSusChem 2019; 12: 3037

13a Li J, Zhang X, Xiang H, Tong L, Feng F, Xie H, Ding J, Yang C. J. Org. Chem. 2017; 82: 6795
13b Zhang X, Yang C. Adv. Synth. Catal. 2015; 357: 2721
13c Xiang H, Yang C. Org. Lett. 2014; 16: 5686

14a Karnakanti S, Zang ZL, Zhao S, Shao PL, Hu P, He Y. Chem. Commun. 2017; 53: 11205
14b Xu J, Qiao L, Shen J, Chai K, Shen C, Zhang P. Org. Lett. 2017; 19: 5661
14c Landge VG, Midya SP, Rana J, Shinde DR, Balaraman E. Org. Lett. 2016; 18: 5252
14d Yu X, Yang F, Wu Y, Wu Y. Org. Lett. 2019; 21: 1726
14e Rej S, Chatani N. ACS Catal. 2018; 8: 6699
14f Parella R, Babu SA. J. Org. Chem. 2017; 82: 6550
14g Mao CL, Zhao S, Zang ZL, Xiao L, Zhou CH, He Y, Cai GX. J. Org. Chem. 2020; 85: 774
14h Aleman-Ponce de Leon D, Sanchez-Chavez AC, Polindara-Garcia LA. J. Org. Chem. 2019; 84: 12809
14i Lukasevics L, Cizikovs A, Grigorjeva L. Org. Lett. 2020; 22: 2720
14j Kuai C, Wang L, Li B, Yang Z, Cui X. Org. Lett. 2017; 19: 2102
14k Biswas S, Bheemireddy NR, Bal M, Van Steijvoort BF, Maes BU. W. J. Org. Chem. 2019; 84: 13112

15a Usui K, Haines BE, Musaev DG, Sarpong R. ACS Catal. 2018; 8: 4516
15b He G, Lu C, Zhao Y, Nack WA, Chen G. Org. Lett. 2012; 14: 2944

16a Kreutter KD, Lu T, Lee L, Giardino EC, Patel S, Huang H, Xu G, Fitzgerald M, Haertlein BJ, Mohan V, Crysler C, Eisennagel S, Dasgupta M, McMillan M, Spurlino JC, Huebert ND, Maryanoff BE, Tomczuk BE, Damiano BP, Player MR. Bioorg. Med. Chem. Lett. 2008; 18: 2865
16b Mizuta S, Stenhagen IS. R, O’Duill M, Wolstenhulme J, Kirjavainen AK, Forsback SJ, Tredwell M, Sandford G, Moore PR, Huiban M, Luthra SK, Passchier J, Solin O, Gouverneur V. Org. Lett. 2013; 15: 2648

Zusatzmaterial

Supporting Information (PDF)