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14. Literature methods for making primary and secondary indole acetamides include amination of the acid chloride or methyl ester. See: (a) Weller, L. E.; Sell, H. M. J. Org. Chem. 1958, 23, 1776. El-Gendy, A. A.; Osman, A. N.; Khalifa, M. Pharmazie 1982, 37, 481.
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14. Literature methods for making primary and secondary indole acetamides include amination of the acid chloride or methyl ester. See: (a) Weller, L. E.; Sell, H. M. J. Org. Chem. 1958, 23, 1776. El-Gendy, A. A.; Osman, A. N.; Khalifa, M. Pharmazie 1982, 37, 481.
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0020622035
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15. Rooney, C. S.; Randall, W. C.; Stneeter, K. B.; Ziegler, C.; Cragoe, E. J.; Schwam, H.; Michelson, S. R.; Williams, H. W. R.; Eichler, E.; Duggan, D. E.; Ulm, E. H.; Noll, R. M. J. Med. Chem. 1983, 26, 700. Fairly fresh potassium t-butoxide was necessary for the reaction to go to completion. The presence of hydroxide ion prevents complete reaction and 5 is difficult to separate from 6. The reaction worked equally well on secondary amides (obtained from the succinimide ester of indole acetic acid).
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27
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0010738467
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-
note
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5S: C, 46.40; H, 2.86 N, 7.21. Found: C, 46.65; H, 3.06; N, 7.05.
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29
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33751385493
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18. Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201.
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31
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33751158485
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McClure, L.D.3
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32
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0010698210
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note
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4S: C, 68.35; H, 4.55; N, 8.25. Found: C, 68.51; H, 4.60; N, 8.17.
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