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Synlett

Volumn , Issue 5, 2009, Pages 0838-0842

Regioselective Sonogashira reactions of N-methyltetrabromopyrrole: First synthesis of tri- and tetra(1-alkynyl)pyrroles

(5) Ullah, Farman a Dang, Tung T b Heinicke, Joachim a Villinger, Alexander b Langer, Peter b

a UNIVERSITY OF GREIFSWALD (Germany)

b UNIVERSITY OF ROSTOCK (Germany)

Author keywords

Carbon carbon bond formation; Catalysis; Palladium; Pyrroles; Regioselectivity

Indexed keywords

EID: 62349105128 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087947 Document Type: Article

Times cited : (18)

References (61)

1
- 0003989710
- Hopf, H, Ed, Wiley-VCH: Weinheim, Chap. 15, and references cited therein
- Classics in Hydrocarbon Chemistry; Hopf, H., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 15, and references cited therein.
- (2000) Classics in Hydrocarbon Chemistry

2
- 84985634908
- Diercks, R.; Armstrong, J. C.; Boese, R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1986, 25, 268.
- (1986) Angew. Chem., Int. Ed. Engl , vol.25 , pp. 268
- Diercks, R.¹ Armstrong, J.C.² Boese, R.³ Vollhardt, K.P.C.⁴

3
- 2242437599
- Neenan, T. X.; Whitesides, G. M. J. Org. Chem. 1988, 53, 2489.
- (1988) J. Org. Chem , vol.53 , pp. 2489
- Neenan, T.X.¹ Whitesides, G.M.²

4
- 0037202218
- Eichhorn, S. H.; Paraskos, A. J.; Kishikawa, K.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 12742.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 12742
- Eichhorn, S.H.¹ Paraskos, A.J.² Kishikawa, K.³ Swager, T.M.⁴

5
- 0000354913
- Bird, C. W, Cheeseman, G. W. H, Eds, Pergamon Press: Oxford
- (a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry, Vol. 4; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon Press: Oxford, 1984, 331.
- (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 331
- Sundberg, R.J.¹

6
- 0001275286
- Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Elsevier: Oxford
- (b) Gribble, G. W. Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Oxford, 1996, 207.
- (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 207
- Gribble, G.W.¹

7
- 0004267670
- Jones, R. A, Ed, Wiley: New York
- (c) Bean, G. P. Pyrroles; Jones, R. A., Ed.; Wiley: New York, 1990, 105.
- (1990) Pyrroles , pp. 105
- Bean, G.P.¹

8
- 0003943783
- Springer: Vienna
- (d) Falk, H. The Chemistry of Linear Oligopyrroles and Bile Pigments; Springer: Vienna, 1989, 355.
- (1989) The Chemistry of Linear Oligopyrroles and Bile Pigments , pp. 355
- Falk, H.¹

9
- 0022345619
- (e) Montforts, F.-P.; Schwartz, U. M. Angew. Chem., Int. Ed. Engl. 1985, 24, 775.
- (1985) Angew. Chem., Int. Ed. Engl , vol.24 , pp. 775
- Montforts, F.-P.¹ Schwartz, U.M.²

10
- 0021087633
- (f) Dutton, C. J.; Fookes, C. J. R.; Battersby, A. R. J. Chem. Soc., Chem. Commun. 1983, 1237.
- (1983) J. Chem. Soc., Chem. Commun , pp. 1237
- Dutton, C.J.¹ Fookes, C.J.R.² Battersby, A.R.³

11
- 0018252180
- (g) Stork, G.; Nakahara, Y.; Nakahara, Y.; Greenlee, W. J. J. Am. Chem. Soc. 1978, 100, 7775.
- (1978) J. Am. Chem. Soc , vol.100 , pp. 7775
- Stork, G.¹ Nakahara, Y.² Nakahara, Y.³ Greenlee, W.J.⁴

12
- 0000478322
- (h) Stork, G.; Nakamura, E. J. Am. Chem. Soc. 1983, 105, 5510.
- (1983) J. Am. Chem. Soc , vol.105 , pp. 5510
- Stork, G.¹ Nakamura, E.²

13
- 0141742509
- For a review of pyrroleimidazole alkaloids, see
- (i) For a review of pyrroleimidazole alkaloids, see: Hoffmann, H.; Lindel, T. Synthesis 2003, 1753.
- (2003) Synthesis , pp. 1753
- Hoffmann, H.¹ Lindel, T.²

14
- 77953502940
- (a) Huisgen, R.; Gotthard, H.; Bayer, H. O.; Schäfer, F. C. Chem. Ber. 1970, 103, 2611.
- (1970) Chem. Ber , vol.103 , pp. 2611
- Huisgen, R.¹ Gotthard, H.² Bayer, H.O.³ Schäfer, F.C.⁴

15
- 37049075412
- (b) Chiu, P.-K.; Lui, K.-H.; Maini, P. N.; Sammes, M. P. J. Chem. Soc., Chem. Commun. 1987, 109.
- (1987) J. Chem. Soc., Chem. Commun , pp. 109
- Chiu, P.-K.¹ Lui, K.-H.² Maini, P.N.³ Sammes, M.P.⁴

16
- 0025016417
- (c) Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587.
- (1990) Tetrahedron , vol.46 , pp. 7587
- Barton, D.H.R.¹ Kervagoret, J.² Zard, S.Z.³

17
- 0000530604
- (d) Roskamp, E. J.; Dragovich, P. S.; Hartung, J. B.; Pederson, S. F. J. Org. Chem. 1989, 54, 4736.
- (1989) J. Org. Chem , vol.54 , pp. 4736
- Roskamp, E.J.¹ Dragovich, P.S.² Hartung, J.B.³ Pederson, S.F.⁴

18
- 0028582111
- (e) Tang, J.; Verkade, J. G. J. Org. Chem. 1994, 59, 7793.
- (1994) J. Org. Chem , vol.59 , pp. 7793
- Tang, J.¹ Verkade, J.G.²

19
- 0031562377
- (f) De Kimpe, N.; Tehrani, K. A.; Stevens, C.; De Cooman, P. Tetrahedron 1997, 53, 3693.
- (1997) Tetrahedron , vol.53 , pp. 3693
- De Kimpe, N.¹ Tehrani, K.A.² Stevens, C.³ De Cooman, P.⁴

20
- 0033591154
- (g) Alberala, A.; Ortega, A. G.; Sádaba, M. L.; Snudo, C. Tetrahedron 1999, 55, 6555.
- (1999) Tetrahedron , vol.55 , pp. 6555
- Alberala, A.¹ Ortega, A.G.² Sádaba, M.L.³ Snudo, C.⁴

21
- 0034697488
- (h) Grigg, R.; Savic, V. Chem. Commun. 2000, 873.
- (2000) Chem. Commun , pp. 873
- Grigg, R.¹ Savic, V.²

22
- 0033781881
- (i) Trofimov, B. A.; Tarasova, O. A.; Mikhaleva, A. I.; Kalinina, N. A.; Sinegovskaya, L. M.; Henkelmann, J. Synthesis 2000, 1585.
- (2000) Synthesis , pp. 1585
- Trofimov, B.A.¹ Tarasova, O.A.² Mikhaleva, A.I.³ Kalinina, N.A.⁴ Sinegovskaya, L.M.⁵ Henkelmann, J.⁶

23
- 0035874693
- (j) Nair, V.; Vinod, A. U.; Rajesh, C. J. Org. Chem. 2001, 66, 4427.
- (2001) J. Org. Chem , vol.66 , pp. 4427
- Nair, V.¹ Vinod, A.U.² Rajesh, C.³

24
- 0035962832
- (k) Ranu, B. C.; Hajra, A. Tetrahedron 2001, 57, 4767.
- (2001) Tetrahedron , vol.57 , pp. 4767
- Ranu, B.C.¹ Hajra, A.²

25
- 0035959503
- (l) Lagu, B.; Pan, M.; Wachter, M. P. Tetrahedron Lett. 2001, 42, 6027.
- (2001) Tetrahedron Lett , vol.42 , pp. 6027
- Lagu, B.¹ Pan, M.² Wachter, M.P.³

26
- 0036394584
- (m) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214.
- (2002) Chem. Commun , pp. 2214
- Quiclet-Sire, B.¹ Wendeborn, F.² Zard, S.Z.³

27
- 0037010759
- (n) Demir, A. S.; Akhmedov, I. M.; Sesenoglu, Tetrahedron 2002, 58, 9793.
- (2002) Tetrahedron , vol.58 , pp. 9793
- Demir, A.S.¹ Akhmedov, I.M.² Sesenoglu³

28
- 0242381768
- (o) Yoshida, M.; Kitamura, M.; Narasaka, K. Bull. Chem. Soc. Jpn. 2003, 76, 2003.
- (2003) Bull. Chem. Soc. Jpn , vol.2003 , pp. 76
- Yoshida, M.¹ Kitamura, M.² Narasaka, K.³

29
- 0242659863
- (p) Knight, D. W.; Sharland, C. M. Synlett 2003, 2258.
- (2003) Synlett , pp. 2258
- Knight, D.W.¹ Sharland, C.M.²

30
- 0346025399
- (q) Yu, M.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099.
- (2003) Org. Lett , vol.5 , pp. 5099
- Yu, M.¹ Pagenkopf, B.L.²

31
- 0346456927
- (r) Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc. 2004, 126, 468.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 468
- Dhawan, R.¹ Arndtsen, B.A.²

32
- 1942456832
- (s) Flögel, O.; Reissig, H.-U. Synlett 2004, 895.
- (2004) Synlett , pp. 895
- Flögel, O.¹ Reissig, H.-U.²

33
- 1942536067
- (t) Song, Z.; Reiner, J.; Zhao, K. Tetrahedron Lett. 2004, 45, 3953.
- (2004) Tetrahedron Lett , vol.45 , pp. 3953
- Song, Z.¹ Reiner, J.² Zhao, K.³

34
- 4444379029
- (u) Chien, T.-C.; Meade, E. A.; Hinkley, J. M.; Townsend, L. B. Org. Lett. 2004, 6, 2857.
- (2004) Org. Lett , vol.6 , pp. 2857
- Chien, T.-C.¹ Meade, E.A.² Hinkley, J.M.³ Townsend, L.B.⁴

35
- 4444383357
- (v) Ramanathan, B.; Keith, A. J.; Armstrong, D.; Odom, A. L. Org. Lett. 2004, 6, 2957.
- (2004) Org. Lett , vol.6 , pp. 2957
- Ramanathan, B.¹ Keith, A.J.² Armstrong, D.³ Odom, A.L.⁴

36
- 1842839853
- (w) Trofimov, B. A.; Zaitsev, A. B.; Schmidt, E. Y.; Vasil'tsov, A. M.; Mikhaleva, A. I.; Ushakov, I. A.; Vashchenko, A. V.; Zorina, N. V. Tetrahedron Lett. 2004, 45, 3789.
- (2004) Tetrahedron Lett , vol.45 , pp. 3789
- Trofimov, B.A.¹ Zaitsev, A.B.² Schmidt, E.Y.³ Vasil'tsov, A.M.⁴ Mikhaleva, A.I.⁵ Ushakov, I.A.⁶ Vashchenko, A.V.⁷ Zorina, N.V.⁸

37
- 9144259637
- (x) Agarwal, S.; Knölker, H.-J. Org. Biomol. Chem. 2004, 2, 3060.
- (2004) Org. Biomol. Chem , vol.2 , pp. 3060
- Agarwal, S.¹ Knölker, H.-J.²

38
- 8644273124
- (y) Dieltiens, N.; Stevens, C. V.; De Vos, D.; Allaert, B.; Drozdzak, R.; Verpoort, F. Tetrahedron Lett. 2004, 45, 8995.
- (2004) Tetrahedron Lett , vol.45 , pp. 8995
- Dieltiens, N.¹ Stevens, C.V.² De Vos, D.³ Allaert, B.⁴ Drozdzak, R.⁵ Verpoort, F.⁶

39
- 27244462040
- Reviews: a
- Reviews: (a) Bäuerle, P. Adv. Mater. 1993, 5, 879.
- (1993) Adv. Mater , vol.5 , pp. 879
- Bäuerle, P.¹

40
- 0342517062
- (b) Tour, J.-M. Chem. Rev. 1996, 96, 537.
- (1996) Chem. Rev , vol.96 , pp. 537
- Tour, J.-M.¹

41
- 4243893235
- (c) Roncali, J. Chem. Rev. 1992, 92, 711.
- (1992) Chem. Rev , vol.92 , pp. 711
- Roncali, J.¹

42
- 20444383861
- (a) Yasuda, T.; Imase, T.; Nakamura, Y.; Yamamoto, T. Macromolecules 2005, 38, 4687.
- (2005) Macromolecules , vol.38 , pp. 4687
- Yasuda, T.¹ Imase, T.² Nakamura, Y.³ Yamamoto, T.⁴

43
- 0347651908
- (b) Ono, N.; Yamamoto, T.; Shimada, N.; Kuroki, K.; Wada, M.; Utsunomiya, R.; Yano, T.; Uno, H.; Murashima, T. Heterocycles 2003, 61, 433.
- (2003) Heterocycles , vol.61 , pp. 433
- Ono, N.¹ Yamamoto, T.² Shimada, N.³ Kuroki, K.⁴ Wada, M.⁵ Utsunomiya, R.⁶ Yano, T.⁷ Uno, H.⁸ Murashima, T.⁹

44
- 0001123553
- (a) Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski, J. M. J. Org. Chem. 1992, 57, 1653.
- (1992) J. Org. Chem , vol.57 , pp. 1653
- Alvarez, A.¹ Guzman, A.² Ruiz, A.³ Velarde, E.⁴ Muchowski, J.M.⁵

45
- 0344002708
- (b) Liu, J.-H.; Chan, H.-W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3274.
- (2000) J. Org. Chem , vol.65 , pp. 3274
- Liu, J.-H.¹ Chan, H.-W.² Wong, H.N.C.³

46
- 37049066387
- (c) Sugihara, Y.; Miyatake, R.; Murata, I.; Imamura, A. J. Chem. Soc., Chem. Commun. 1995, 1249.
- (1995) J. Chem. Soc., Chem. Commun , pp. 1249
- Sugihara, Y.¹ Miyatake, R.² Murata, I.³ Imamura, A.⁴

47
- 0003660996
- Reviews: a, Pergamon Press: Oxford
- Reviews: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon Press: Oxford, 2000.
- (2000) Palladium in Heterocyclic Chemistry
- Li, J.J.¹ Gribble, G.W.²

48
- 0026545386
- (b) Kalinin, V. N. Synthesis 1992, 413.
- (1992) Synthesis , pp. 413
- Kalinin, V.N.¹

49
- 13644268558
- Review
- Review: Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245.
- (2005) Tetrahedron , vol.61 , pp. 2245
- Schröter, S.¹ Stock, C.² Bach, T.³

50
- 23644459450
- Schröter, S.; Bach, T. Synlett 2005, 1957.
- (2005) Synlett , pp. 1957
- Schröter, S.¹ Bach, T.²

51
- 33845877985
- Dang, T. T.; Rasool, N.; Dang, T. T.; Reinke, H.; Langer, P. Tetrahedron Lett. 2007, 48, 845.
- (2007) Tetrahedron Lett , vol.48 , pp. 845
- Dang, T.T.¹ Rasool, N.² Dang, T.T.³ Reinke, H.⁴ Langer, P.⁵

52
- 38949159647
- Dang, T. T.; Dang, T. T.; Ahmad, R.; Reinke, H.; Langer, P. Tetrahedron Lett. 2008, 49, 1698.
- (2008) Tetrahedron Lett , vol.49 , pp. 1698
- Dang, T.T.¹ Dang, T.T.² Ahmad, R.³ Reinke, H.⁴ Langer, P.⁵

53
- 0000113044
- Gilow, H. M.; Burton, D. E. J. Org. Chem. 1981, 46, 2221.
- (1981) J. Org. Chem , vol.46 , pp. 2221
- Gilow, H.M.¹ Burton, D.E.²

54
- 62349109811
- General Procedure for Sonogashira Reactions Tetrabromo-N-methylpyrrole (1, 750 mg, 1.87 mmol, Ph3P (98 mg, 20 mol, PdCl2 (MeCN)2 (49 mg, 10 mol, and CuI (36 mg, 10 mol, were added to an oven-dried Schlenk flask, evacuated for 10 min, and then flushed with argon. To the mixture was added thoroughly dried, freshly distilled and oxygen-free diisopropylamine (20 mL, The clear yellow solution was stirred for 15 min at 20°C for the generation of the catalyst. The solution was subsequently cooled to 0°C, and the alkyne was dropwise added by syringe. The solution was stirred for 1 h at 0°C and for 3 h at 20°C. The dark brown mixture was heated at 90°C. The solution was allowed to cool to ambient temperature, filtered, and the filtrate was concentrated in vacuo. To the residue was added CH2Cl2, and the solution was extracted with H2O. The combined organic layers were dried MgSO
- 4), filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (neutral silica gel, n-hexane). For the synthesis of products 3, the two alkynes were added at the same time.

55
- 62349121719
- Synthesis of 2a Starting with 1 (500 mg, 1.25 mmol) and 2-pentyne (1.3 mmol, 2a was isolated (134 mg, 30, as a brownish highly viscous oil. 1H NMR (250 MHz, CDCl3, δ, 1.06 (t, 3J, 7.5 Hz, 3 H, Me, 1.64 (sext, 3J, 7.2 Hz, 2 H, CH2, 2.47 (t, 3J, 7.0 Hz, 2 H, CH 2, 3.64 (s, 3 H, NCH3, 13C NMR (62.8 MHz, CDCl3, δ, 13.5 (CH3, 21.6, 22.0 (CH2, 35.6 (NCH3, 70.1, 98.8 (C≡C, 100.4, 102.93, 104.19, 118.34 (C, pyrrole, IR (KBr, 3436 (br, s, 2958 (s, 2932 (m, 2872 (m, 2228 (w, 1717 (m, 1529 (m, 1456 (s, 1431 (m, 1378 (m, 1330 (s, 1092 (m) cm -1. MS (EI, 70 eV, 85°C, m/z, 381 (19, M, 79Br, 79Br, 79Br, 356 (67, 354 (58, 275 (14, 224 (54, 194 (60, 115 100, HRMS: m/z calcd for C
- 79Br]: 380.83579; found: 380.83501.

56
- 62349084490
- Synthesis of 3c Starting with 1 (500 mg, 1.25 mmol, 2-methyl-3-pentyne-2-ol (1.3 mmol, and p-tolylacetylene (1.3 mmol, 3c was isolated (238 mg, 44, as a red to brown solid. 1H NMR (250 MHz, CDCl3, δ, 1.65 (s, 6 H, CH3, 2.36 (s, 3 H, Metolyl, 3.72 (s, 3 H, CH3, 7.16 (d, 3J, 8.1 Hz, 2 H, tolyl, 7.43 (d, 3J, 8.1 Hz, 2 H, tolyl, 13C NMR (62.8 MHz, CDCl3, δ, 21.6 (CH3, tolyl, 31.3 (CH3, 34.4 (NCH3, 65.9 (C, CMe 2OH, 71.7, 71,6 (C≡C, 97.5, 97.7 (C, pyrrole, 102.2, 103.9 (C≡C, 116.9, 117.9 (C, pyrrole, 119.1, 131.4 (CH, p-tolyl, 139.2 (C, p-tolyl, IR (KBr, 3324 (br, s, 2983 (s, 2929 (s, 2865 (w, 2249 (m, 1906 (w, 1728 (s, 1534 (m, 1509 (m, 1440 (s, 1232 (s, 1160 (br, s, 910 (s, 815 (s, 730 (br, s) cm-1. MS EI, 70 eV, 110°C
- 79Br].

57
- 62349090366
- Synthesis of 5b Procedure A16 Starting with 1 (750 mg, 1.87 mmol) and p-tolylacetylene (0.6 mL, 4.67 mmol, 5b (620 mg, 71, was isolated as a white solid. 1H NMR (250 MHz, CDCl3, δ, 2.36 (s, 6 H, CH3, p-tolyl, 3.77 (s, 3 H, NCH3, 7.14 (d, 3J, 8.1 Hz, 4 H, p-tolyl, 7.56 (d, 3J, 8.1 Hz, 4 H, p-tolyl, 13C NMR (62.8 MHz, CDCl3, δ, 21.6 (CH3, p-tolyl, 34.6 (NCH3, 77.9 (C≡C, 97.7 (C, pyrrole, 104.1 (C≡C, 117.9 (C, pyrrole, 119.1 (C, p-tolyl, 129.2 (CH, p-tolyl, 131.3 (CH, p-tolyl, 139.1 (C, p-tolyl, IR (KBr, 3435 (br, m, 3023 (m, 2717 (s, 2206 (w, 1537 (s, 1441 (s, 1377 (s, 1345 (s, 817 (s, 809 (8 s, 535 (s, 520 (s) cm-1. MS (EI, 70 eV, 320°C, m/z, 465.6 51, M, 79Br, 7
- 2N: 464.97223; found: 464.97163.

58
- 33947416063
- and references cited therein
- Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358; and references cited therein.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 3358
- Billingsley, K.¹ Buchwald, S.L.²

59
- 62349131931
- CCDC-689251 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk.
- CCDC-689251 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk.

60
- 62349136328
- Synthesis of 8c Starting with 1 (500 mg, 1.25 mmol) and 2-methyl-3-pentyne-2-ol (0.4 mL, 4.12 mmol, 8c was isolated (198 mg, 40, as a brownish solid. 1H NMR (250 MHz, DMSO-d 6, δ, 1.45, s, 12 H, 4 CH3, 1.48 (s, 6 H, 2 CH3, 3.60 (s, 3 H, NCH3, 5.42, 5.60, 5.61 (3 s, 3 OH, 13C NMR (62.8 MHz, DMSO-d6, δ, 31.35, 31.38, 31.8, 6 CH3, 33.8 (NCH3, 63.8, 63.9, C, CMe2OH, 69.8, 70.0, 72.4, C≡C, 100.1, 102.6, 103.7 (C, pyrrole, 104.1, 110.0 (C≡C, 116.8 (C, pyrrole, 119.9 (C, pyrrole, IR (KBr, 3435 (br, s, 2980 (s, 2933 (s, 2226 (w, 1634 (m, 1452 (m, 1374 (s, 1374 (s, 1238 (s, 1164 (s, 1137 (s, 989 (w, 938 (s, 939 (m, 892 (w, 841 (m) cm-1. MS (EI, 70 eV, 130°C, m/z, 405 (99, M, 79Br, 403 (16, 390 (14, 388 (28, 374 (65, 372 71, 27
- 79Br]: 405.09341; found: 405.09328.

61
- 62349104336
- Synthesis of 9a. Starting with 1 (500 mg, 1.25 mmol) and phenylacetylene (0.82 mL, 7.5 mmol, 9a was isolated (150 mg, 25, as an orange-red oil. 1H NMR (250 MHz, CDCl3, δ, 3.81 (s, 3 H, NCH3, 7.32 (br s, 4 H, Ph, 7.35 (m, 8 H, Ph, 7.56 (m, 8 H, Ph, 13C NMR (62.8 MHz, CDCl3, δ, 33.8 (NCH3, 79.2, 82.3, 94.3 (C≡C, 112.7 (C, pyrrole, 120.6 (C, pyrrole, 122.5 (C, Ph, 123.9 (C, Ph, 127.9, 128.3, 128.46, 128.7, 131.46, 131.52 (CH, Ph, IR (KBr, 3435 (m, 3058 (w, 2959 (s, 2927 (s, 2871 (m, 2204 (s, 1728 (s, 1597 (s, 1478 (s, 1454 (s, 1376 (m, 1255 (m, 1067 (m, 910 (m, 754 (s, 688 (s) cm-1. MS (EI, 70 eV, 85°C, m/z, 482 (10, 481 (39, M, 480 (100, 476 (6, 401 (4, 338 (6, 239 (22, 230 2, HRMS: m/z calcd for C37H23N; 481.18301; found: 481.18276
- 23N; 481.18301; found: 481.18276.

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