A Practical, Efficient Synthesis of 5-Amino-7-azaindole

Stuart E. Pearson; Santosh Nandan

doi:10.1055/s-2005-872088

PAPER

A Practical, Efficient Synthesis of 5-Amino-7-azaindole

Stuart E. Pearson*^a, Santosh Nandan^b
^a AstraZeneca Plc., Alderley Park, Macclesfield, Cheshire SK10 4TG, UK
Fax: +44(1625)513910; e-Mail: stuart.pearson@astrazeneca.com;
^b AstraZeneca Pvt. Ltd. (R&D), Bellary Road, Hebbal, Bangalore 560 024, India
Fax: +91(80)23621214; e-Mail: santosh.nandan@astrazeneca.com;

Abstract

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Abstract

A much improved, workable synthesis of 5-amino-7-azaindole is described in 66% overall yield starting from 2-amino-5-nitropyridine. The key stage involves a microwave promoted heteroannulation reaction of a pyridine alkyne.

Key words

azaindoles - alkynes - copper - cyclizations - microwaves

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Referenzen

References

1 Robison MM. Robison BL. Butler FP. J. Am. Chem. Soc. 1959, 81: 743

2 Bhide R, Ruel R, Thibeault C, and L’heureux A. inventors; PCT Int. Appl., WO 2004009601.

3 Poirier J.-M. Vottero C. Tetrahedron 1989, 45: 1415

4a Park SS. Choi J.-K. Yum EK. Ha D.-C. Tetrahedron Lett. 1998, 39: 627

4b Kumar V. Dority JA. Bacon ER. Singh B. Lesher GY. J. Org. Chem. 1992, 57: 6995

4c Wensbo D. Eriksson A. Jeschke T. Annby U. Gronowitz S. Cohen LA. Tetrahedron Lett. 1993, 34: 2823

4d Xu L. Lewis IR. Davidsen SK. Summers JB. Tetrahedron Lett. 1998, 39: 5159

4e Ezquerra J. Pedregal C. Lamas C. Barluenga J. Pérez M. García-Martín MA. González JM. J. Org. Chem. 1996, 61: 5804

5 Batkowski T. Rocz. Chem. 1969, 43: 1623 ; Chem. Abstr. 1969, 72, 21575

6

Compound synthesised on 10-g scale using this method by GVK Biosciences Pvt. Ltd. 210, My Home Tycoon, 6-3-1192, Kundan Bagh, Begumpet, Hyderabad - 500016, India.

7 Taylor EC. Macor JE. Pont JL. Tetrahedron 1987, 43: 5145