Optimization and scale-up of the Grandberg synthesis of 2-methyltryptamine

Organic Process Research and Development

Volumn 11, Issue 4, 2007, Pages 721-725

  Slade, Joel ^a   Parker, David ^a   Girgis, Michael ^a   Wu, Raeann ^a   Joseph, Scott ^a   Repič, Oljan ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

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[No Author keywords available]

Indexed keywords

EID: 34547869768     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op7000518     Document Type: Article

References (10)

1. Yoshida, M.; Nomura, S.; Beppu, T. Cancer Res. 1987, 47, 3688-3691.
2. Itazaki, H.; Nagashima, K.; Sugita, K.; Yoshida, H.; Kawamura, Y.; Yasuda, Y.; Matsumoto, K.; Ishii, K.; Uotani, N.; Nakai, H.; Terui, A.; Yoshuimatsu, S.; Ikenishi, Y.; Nakagawa, Y. J. Antibiot. 1990, 12, 1524-1532.
3. (a) Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons: New York, 1982; pp 487-489.
4. (b) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875-2911.
5. (a) Grandberg, I. I.; Zuyanova, T. I.; Afonia, N. I.; Ivanova, T. A. Dokl. TSKhA 1967, 124, 325.
6. (b) Grandberg, I. I.; Zuyanova, T. I.; Afonina, N. I.; Ivanova, T. A. Dokl. Akad. Nauk SSSR 1967, 176, 583.
7. Subsequent to the completion of our work, a publication appeared in which the Grandberg modification of the Fischer indole synthesis was scaled up in the laboratory as part of the synthesis of PHA-565272-A. See: Fleck, T. J.; Chen, J. J.; Lu, C. V. Org. Process Res. Dev. 2006, 10, 334-38.
8. Granberg, I. I.; Przheval'skii, I. M.; Vysotskii, V. I. Khim. Geterotsikl. Soedin. 1970, 11, 1499-1504.
9. Grandberg, I. I.; Zuyanova, T. I. Khim. Geterosikl. Soedin. 1968, 4(5), 875-877.
10. Pfeil, E.; Harder, U. Angew. Chem. 1967, 79(4), 188-189.