SYNTHESIS OF NEW ACTIVATED INDOLES; 3-(4’-BROMOPHENYL)-4,6-DIMETHOXY-2-METHYLINDOLE

https://doi.org/10.22146/ijc.21853

Tutik Dwi Wahyuningsih(1*)

(1) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
(*) Corresponding Author

Abstract


3-(4'-Bromophenyl)-4,6-dimethoxy-2-methylindole has been synthesized from 4,6-dimethoxyaniline via the modified Bischler method. Reaction of 4,6-dimethoxyaniline with 2,4-dibromopropiophenone gave an aniline ketone in 85%, and then it was protected to give the amido ketone as a white solid. Cyclization of amido ketone was performed by trifluoroacetic acid and subsequent deprotection with potassium hydroxide in methanol afforded a white solid of 3-(4'-bromophenyl)-4,6-dimethoxy-2-methylindole in 86%.


Keywords


4,6-dimethoxyaniline; 2-methylindole; Bischler method

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References

[1]   Nachshon-Kedmi, M., Yannai, S., Haj, A., and Fares, F.A. 2003, Food Chem. Toxicol. 41, 745-752.

[2]   Zheng, Q., Hirose, Y., Yoshimi, N., Murakami, A., Koshimizu, K., Ohigashi, H., Sakata, K., Matsumoto, Y., Sayama, Y., and Mori, H., 2002, J. Can. Res. Clin. Oncol. , 128, 539-546.

[3]   Meng, Q., Goldberg, I.D., Rosen, E.M., and Fan, S., 2000 Breast Cancer Res. Tr., 63, 147-152.

[4]   Winter, C.A., Risley, E.A., and Silber, R.H. 1968, J.  Pharmacol. Exp. Ther., 162, 196-201.

[5]   Kaneda, M., Naid, T., Kitahara, T., Nakamura, S., Hirata, T., and Suga, T., 1988 J. Antibiot., 41, 602-608.

[6]   Brown, V.H., Skinner, W.A., and De Graw, J.I., 1969, J. Heterocycl. Chem., 6, 539-543.

[7]   Black, D.StC., Gatehouse, B.M. K.C., Theobald, F., and Wong, L.C.H., 1980, Aust. J. Chem., 33, 343-350.

[8]   Black, D.StC., Kumar, N., and Wong, L.C.H., 1986, Aust. J. Chem., 39, 15-20.

[9]   Crowther, A.F., Mann, F.G., and Purdie, D., 1943, J. Chem. Soc., 58-68.

[10] Nordlander, J.E., Catalane, D.B., Kotian, K.D., Stevens, R.M., and Haky, J.E., 1981, J. Org. Chem., 46, 778-782.

[11] Black, D.StC., Bowyer, M.C., Bowyer, P.K., Ivory, A.J., Kim, M., Kumar, N., McConnell, D.B., and Popiolek, M. , 1994, Aust. J. Chem., 47, 1741-1750.

[12] Sholihin, H., 1996 Ph.D Thesis, University of New South Wales.



DOI: https://doi.org/10.22146/ijc.21853

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