Green N-methylation of electron deficient pyrroles with dimethylcarbonate

Organic Process Research and Development

Volumn 13, Issue 6, 2009, Pages 1199-1201

  Laurila, Michael L ^a   Magnus, Nicholas A ^a   Staszak, Michael A ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72449195705     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900256t     Document Type: Article

References (11)

1. For examples of the N-methylation of pyrroles and indoles see: (a) Baltazzi, E.; Krimen, L. I. Chem. Rev. 1963, 63 (5), 511.
2. (b) Reinecke, M. G.; Sebastian, J. F.; Johnson, H. W.; Pyun, C. J. Org. Chem. 1972, 37, 3066.
3. (c) Santaniello, E.; Farachi, C.; Ponit, F. Synthesis 1979, 8, 617.
4. (a) Tundo, P.; Selva, M. Methods and Reagents for Green Chemistry. In Chemistry for the Environment; John Wiley and Sons: New Jersey, 2007; Vol. 77, p 102.
5. (b) Chankeshwawa, S. V. Synlett 2008, 4, 624.
6. (c) Rekha, V. V.; Ramani, M. V.; Ratnamala, A.; Rupakalpana, V.; Subbaraju, V.; Satyanarayana, C.; Rao, C. S. Org. Process Res. Dev. 2009, 13, 769-3.
7. Magnus, N. A.; Staszak, M. A.; Udodong, U. E.; Wepsiec, J. P. Org. Process Res. Dev. 2006, 10, 899.
8. (a) Jiang, X.; Tiwari, A.; Thompson, M.; Chen, Z.; Cleary, T. P.; Lee, T. B. Org. Process Res. Dev 2001, 5, 604.
9. (b) Shieh, W. C.; Dell, S.; Bach, A.; Repič, O.; Blacklock, T. J. J. Org. Chem. 2003, 68 (5), 1954.
10. (a) Quaranta, E.; Carafa, M.; Trani, F. Appl. Catal., B 2009, 91, 380.
11. (b) Ouk, S.; Thiebaud, S.; Borredon, E. Synth. Commun. 2005, 35, 3021.