2438
Y. R. Jorapur et al. / Tetrahedron Letters 47 (2006) 2435–2438
16. (a) Nunomoto, S.; Kawakami, Y.; Yamashita, Y.; Take-
uchi, H.; Eguchi, S. J. Chem. Soc., Perkin Trans. 1 1990,
111–114; (b) Earle, M. J.; McCormac, P. B.; Seddon, K.
R. Chem. Commun. 1998, 2245–2246.
carried out at the Korea Basic Science Institute (Daegu,
Korea).
17. Jorapur, Y. R.; Lee, C. H.; Chi, D. Y. Org. Lett. 2005, 7,
1231–1234.
18. Jorapur, Y. R.; Chi, D. Y. J. Org. Chem. 2005, 70, 10774–
10777.
Supplementary data
Characterization of all compounds including 1H and 13
NMR spectra (16 pages). Supplementary data associ-
ated with this article can be found, in the online version,
C
19. Typical procedure: Potassium carbonate (345 mg,
2.5 mmol), indole (7, 1.0 mmol), [bmim][BF4] (2.0 mL),
and CH3CN (1.0 mL) were stirred over 10 h at 110 ꢁC. The
reaction mixture was cooled to room temperature.
1-Bromo-3-phenylpropane (2a, 398 mg, 2.0 mmol) was
added to the reaction mixture and stirred for another
24 h at 110 ꢁC. The reaction was monitored by thin layer
chromatography (TLC) until trace or no indole was
observed. The reaction mixture was extracted from ionic
liquid phase with ethyl ether (10 mL · 5). The organic layer
was dried over anhydrous sodium sulfate and evaporated
under reduced pressure. The residue was purified by flash
column chromatography (10% EtOAc/Hx) to obtain
193 mg (82%) of 1-(3-phenylpropyl)-1H-indole (8) as
colorless oil. In case of pyrrole N-alkylation the procedure
was the same except pyrrole (1, 2.0 mmol), and 1-bromo-3-
phenylpropane (2a, 796 mg, 4.0 mmol) were used. Reac-
tion mixture was stirred over 30 h at 110 ꢁC.
References and notes
1. (a) Jiang, S.; Lu, H.; Liu, S.; Zhao, Q.; He, Y.; Debnath,
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201–208; (c) The Alkaloids; Manske, R. H. F., Ed.; Wiley:
New York, 1950–1970; pp 1–17; (d) Hesse, H. Indol
Alkaloide in Tabellen; Springer: Berlin, 1964.
2. (a) Gribble, G. W. Prog. Chem. Org. Nat. Prod. 1996, 68,
133–141; (b) Evans, L. S.; Tramontano, W. A.; Gill, R.
Phytochemistry 1987, 26, 2891–2893; (c) Kyburz, R.;
Schoepp, E.; Bick, I.; Ralph, C.; Hesse, M. Helv. Chim.
Acta 1979, 62, 2539–2546; (d) Mattocks, A. R.; Driver, H.
E. Toxicology 1983, 27, 159–177; (e) Rawal, V. H.; Jones,
R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 19–28.
3. Kato, M.; Komoda, K.; Namera, A.; Sakai, Y.; Okada, S.;
Yamada, A.; Yokoyama, K.; Migita, E.; Minobe, Y.;
Tani, T. Chem. Pharm. Bull. 1997, 45, 1767–1776.
4. Comprehensive Medicinal Chemistry; Sammes, P. G.,
Taylor, S. B., Eds.; Pergamon Press: Oxford, 1990; Vol.
6, p 280, 403, 613, 801, 951, and 963.
5. Hobbs, C. F.; McMillin, C. K.; Papadopoulos, E. P.;
VanderWerf, C. A. J. Am. Chem. Soc. 1962, 84, 43–51.
6. Jones, R. A.; Bean, G. P. In The Chemistry of Pyrroles;
Blomquist, A. T., Wasserman, H. H., Eds.; Academic
Press: London, 1977; Vol. 34, p 173.
7. Heaney, H.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1
1973, 5, 499–500.
8. Yim, E. S.; Park, M. K.; Han, B. H. Ultrason. Sonochem.
1997, 4, 95–98.
1-(3-Phenylpropyl)-1H-indole (8): Colorless liquid; 1H
NMR (400 MHz, CDCl3) d 2.20 (quin, J = 7.2 Hz, 2H),
2.65 (t, J = 7.6 Hz, 2H), 4.15 (t, J = 7.2 Hz, 2H), 6.52
(d, J = 2.0 Hz, 1H), 7.10–7.34 (m, 9H), 7.66 (d, J = 4.4 Hz,
1H); 13C NMR (100 MHz, CDCl3) d 31.4, 32.9, 45.6, 101.0,
109.3, 119.2, 120.9, 121.3, 126.1, 127.7, 128.4, 128.5, 128.6,
135.9, 140.9; MS (EI) 235 (M+), 130 (100). Anal. Calcd: C,
86.77; H, 7.28; N, 5.95. Found: C, 86.73; H, 7.22; N, 6.35.
3-Phenylpropyl-1H-indole-1-carboxylate (9): Colorless
liquid; 1H NMR (400 MHz, CDCl3)
d 2.18 (quin,
J = 8.0 Hz, 2H), 2.83 (t, J = 8.0 Hz, 2H), 4.46 (t, J =
6.8 Hz, 2H), 6.61–6.62 (m, 1H), 7.20–7.38 (m, 9H), 8.19–
8.21 (m, 1H); 13C NMR (100 MHz, CDCl3) d 30.3, 32.2,
66.4, 108.0, 115.1, 121.0, 123.0, 124.5, 125.5, 126.2, 128.4,
128.45, 130.5, 135.2, 140.8, 151.0; MS (EI) 279 (M+), 91
(100). HR MS (EI) calcd for C18H17NO2 (M+) 279.1259,
found 279.1262.
9. (a) Szmuzkovicz, J. Belg. Pat. 621,047, 1963; (b) Giles, P.
R.; Rogers-Evans, M.; Soukup, M.; Knight, J. Org.
Process Res. Dev. 2003, 7, 22–24.
10. Girard, M.; Hamel, P. J. Org. Chem. 2000, 65, 3123–3125.
11. (a) Normant, H.; Cuvigny, T. Bull. Soc. Chim. Fr. 1965,
1866–1872; (b) Rubottom, G. M.; Chabala, J. C. Org. Syn.
1974, 54, 60–62.
1-Biphenyl-4-ylmethyl-1H-pyrrole (10): White solid; mp
102–103 ꢁC; H NMR (400 MHz, CDCl3) d 5.12 (s, 2H),
1
6.22 (t, J = 2.4 Hz, 2H), 6.74 (t, J = 2.0 Hz, 2H), 7.18–7.20
(m, 2H), 7.35–7.37 (m, 1H), 7.42–7.46 (m, 2H), 7.54–7.58
(m, 4H); 13C NMR (100 MHz, CDCl3) d 53.03, 108.5,
121.1, 127.0, 127.3, 127.4, 127.45, 128.8, 137.2, 140.6; MS
(EI) 233 (M+), 167 (100). Anal. Calcd: C, 87.52; H, 6.48; N,
6.00. Found: C, 87.81; H, 6.72; N, 6.35.
12. Fink, D. M. Synlett 2004, 2394–2396.
13. (a) Bocchi, V.; Casnati, G.; Dossena, A.; Villani, F.
Synthesis 1976, 414–416; (b) Santaniello, E.; Farachi, C.;
Ponti, F. Synthesis 1979, 617–618.
14. For reviews, see: (a) Sheldon, R. Chem. Commun. 2001,
2399–2407; (b) Wasserscheid, P. J.; Keim, W. Angew.
Chem., Int. Ed. 2000, 39, 3772–3789; (c) Welton, T. Chem.
Rev. 1999, 99, 2071–2083.
15. (a) Kim, D. W.; Song, C. E.; Chi, D. Y. J. Am. Chem. Soc.
2002, 124, 10278–10279; (b) Kim, D. W.; Song, C. E.; Chi,
D. Y. J. Org. Chem. 2003, 68, 4281–4285; (c) Kim, D. W.;
Choe, Y. S.; Chi, D. Y. Nucl. Med. Biol. 2003, 30, 345–
350; (d) Kim, D. W.; Hong, D. J.; Seo, J. W.; Kim, H. S.;
Kim, H. G.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2004,
69, 3186–3189; (e) Boovanahalli, S. K.; Kim, D. W.; Chi,
D. Y. J. Org. Chem. 2004, 69, 4945–4951.
9-(3-Phenylpropyl)-9H-carbazole (14): Yellow solid; mp
111–112 ꢁC; 1H NMR (400 MHz, CDCl3) d 2.20 (quin,
J = 7.6 Hz, 2H), 2.70 (t, J = 8.0 Hz, 2H), 4.30 (t, J =
7.2 Hz, 2H), 7.15–7.46 (m, 11H), 8.09–8.10 (m, 2H); 13C
NMR (100 MHz, CDCl3) d 30.1, 33.3, 42.4, 108.6, 118.8,
120.3, 122.8, 125.5, 126.1, 128.3, 128.4, 140.3, 141.0; MS
(EI) 285 (M+), 180 (100). Anal. Calcd: C, 88.38; H, 6.71; N,
4.91. Found: C, 88.14; H, 6.99; N, 4.61.
20. Ionic liquid recycling procedure: To the ionic liquid phase
ethyl acetate (5.0 mL) was added and filtered. The filtrate
was washed with water (2.0 mL · 4). The organic layer
was dried over anhydrous magnesium sulfate and evapo-
rated under reduced pressure. Ionic liquid was further
dried under high vacuum at 80 ꢁC overnight and used for
the next run.