518
Q. Yang et al. / Chinese Chemical Letters 22 (2011) 515–518
General procedure: A mixture of indole (2 mmol), 5 mL of solvent, and 1 mmol of aldehyde or ketone was stirred
for 5 min at room temperature, then 0.1 mmol of pyridinium tribromide was added. The reaction was followed by
TLC. When the reaction was completed, the organic material was extracted with ethyl acetate, washed with water, and
dried over Na SO , and concentrated. The residue was purified by flash chromatography with petroleum/ethyl acetate
2
4
1
13
to give product. All products have been reported in previous literature and confirmed by H NMR and C NMR in this
experiment.
For example, the reaction of p-methylbenzaldehyde and indole gave the corresponding product of the bis(3-
1
indolyl)-tolylmethane (Table 3, entry 13): Pale-red solid, yield 95%, mp 96–97 8C; H NMR (400 MHz, CDCl ): d
3
7
.86 (br s, 2H), 7.38 (d, 2H, J = 8.0 Hz), 7.33 (d, 2H, J = 8.4 Hz), 7.21 (d, 2H, J = 8.0 Hz), 7.15 (t, 2H, J = 7.6 Hz),
1
.07 (d, 2H, J = 8.0 Hz), 6.99 (t, 2H, J = 7.2 Hz), 6.65 (s, 2H), 5.84 (s, 1H), 2.31 (s, 3H); C NMR (100 MHz, CDCl3):
3
7
d 141.0, 136.7, 135.4, 128.9, 128.5, 127.1, 123.5, 121.8, 120.0, 119.9, 119.2, 110.9, 39.8, 21.0.
Acknowledgments
We are grateful to the National Natural Science Foundation of China (Nos. 20862009 and 20962010), the National
Natural Science Foundation of Jiangxi Province (No. 2008GQH0026) and the Science Foundation of Education
Department of Jiangxi Province (No. GJJ10386) for their financial support.
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