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Helvetica Chimica Acta – Vol. 90 (2007)
Table (cont.)
Entry Indole
Olefin
Product
Time [min] Yield [%]a)
17
18
2
5
88
91
a) After column-chromatographic purification. b) Some 10% of the corresponding higher adduct was also
obtained.
1
1-(5-Bromo-1H-indol-3-yl)pentan-3-one (Table, Entry 7). Solid. H-NMR (CDCl3, 200 MHz): 8.04
(br. s, 1 H); 7.70( s, 1 H); 7.31–7.22 (m, 2 H); 7.00 (d, J=1.5, 1 H); 3.02 (t, J=7.0, 2 H); 2.81 (d,
J=7.0, 2 H); 2.42 (q, J=7.0, 2 H); 1.08 (t, J=7.0, 3 H). FAB-MS: 282/280 ([M+H]+). Anal. calc. for
C13H14BrNO: C 55.17, H 5.00, N 5.00; found: C 55.22, H 5.08, N 5.12.
3-(4-Chlorophenyl)-3-(1H-indol-3-yl)-1-phenylpropan-1-one (Table, Entry 10). Solid. 1H-NMR
(CDCl3, 200 MHz): 7.98 (br. s, 1 H); 7.90( d, J=8.0, 1 H); 7.59–7.05 (m, 11 H); 7.03–6.90 (m, 2 H);
5.01 (dd, J=7.0, 5.5, 1 H); 3.78 (dd, J=12.5, 5.5, 1 H); 3.62 (dd, J=12.5, 7.0, 1 H). FAB-MS: 362/360
([M+H]+). Anal. calc. for C23H18ClNO: C 76.77, H 5.01, N 3.89; found: C 76.63, H 5.12, N 3.91.
3-(5-Bromo-1H-indol-3-yl)-3-(4-chlorophenyl)-1-phenylpropan-1-one (Table, Entry 11). Solid. 1H-
NMR (CDCl3, 200 MHz): 7.99 (br. s, 1 H); 7.89 (d, J=8.0, 1 H); 7.56–7.40 (m, 4 H); 7.26–7.13 (m, 7
H); 6.92 (d, J=1.5, 1 H); 4.97 (dd, J=7.0, 5.5, 1 H); 3.71 (dd, J=12.0, 5.5 1 H); 3.61 (dd, J=12.0, 7.0,
1 H). FAB-MS: 442/440/438 ([M+H]+). Anal. calc. for C23H17BrClNO: C 62.97, H 3.88, N 3.19;
found: C 62.91, H 3.82, N 3.23.
5-Bromo-3-(2-nitro-1-phenylethyl)-1H-indole (Table, Entry 17). Solid. 1H-NMR (CDCl3, 200 MHz):
8.28 (br. s, 1 H); 7.50( d, J=1.5, 1 H); 7.45–7.18 (m, 7 H); 7.03 (d, J=1.5, 1 H); 5.11 (dd, J=7.0, 5.5, 1 H);
5.01–4.79 (m, 2 H). FAB-MS: 347/345 ([M+H]+). Anal. calc. for C16H13BrN2O2: C 55.65, H 3.76, N 8.11;
found: C 55.58, H 3.81, N 8.17.
REFERENCES
[1] M. M. Faul, L. L. Winneroski, C. A. Krumrich, J. Org. Chem. 1998, 63, 6053; H.-C. Zhang, H. Ye, A.
F. Moretto, K. K. Brumfield, B. E. Maryanoff, Org. Lett. 2000, 2, 89; C. Aubry, A. Patel, S. Mahale, B.
Chaudhuri, J.-D. Marechal, M. J. Sutcliffe, P. R. Jenkins, Tetrahedron Lett. 2005, 46, 1423; J. J. Maru-
gan, C. Manthey, B. Anaclerio, L. Lafrance, T. Lu, T. Markotan, K. A. Leonard, C. Crysler, S. Eisen-
nagel, M. Dasgupta, B. Tomczuk, J. Med. Chem. 2005, 48, 926.
[2] R. E. Moore, C. Cheuk, G. M. L. Patterson, J. Am. Chem Soc. 1984, 106, 6456; R. E. Moore, C.
Cheuk, X. Q. Yang, G. M. L. Petterson, R. Bonjouklian, T. A. Smitka, J. S. Mynderse, R. S. Foster,
N. D. Jones, J. K. Swartzendruber, J. B. Deeter, J. Org. Chem. 1987, 52, 1036; G. W. Gribble, J.
Chem. Soc., Perkin Trans. 1 2000, 1045.
[3] W. E. Noland, G. M. Christensen, G. L. Sauer, G. G. S. Dutton, J. Am. Chem Soc. 1955, 77, 456; J.
Szmuszkoviez, J. Am. Chem Soc. 1975, 79, 2819; Z. Iqbal, A. H. Jackson, K. R. N. Rao, Tetrahedron
Lett. 1988, 29, 2577.