Traceless solid phase synthesis of indole derivatives

Details Traceless solid phase synthesis of indole derivatives Traceless solid phase synthesis of indole derivatives

1998-09-02

1999-07-06

Ramjuer, Robert W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548504, 548509, 548511, 548506, C07D20914, C07D20912, C07D20908

Patent

active

059199474

ABSTRACT:
The present invention relates to a traceless solid phase process for the preparation of an indole derivative, which comprises the following steps:
(1) reaction of an optionally substituted 2-iodoaniline derivative via the nitrogen atom of the NH.sub.2 moiety thereof with a dihydropyran-functionalized polymeric resin under conditions effective to form an aminal linkage;
(2) reaction of the tetrahydropyran aminal derivative thereby obtained with an acetylene derivative in the presence of a transition metal catalyst under conditions effective to promote indole formation;
(3) treatment of the product thereby obtained with acid, whereby the aminal linkage is cleaved and the desired indole derivative is liberated from the resin; and
(4) isolation of the desired indole derivative thereby obtained.

REFERENCES:
Thompson, Lorin et al., Straightforward and General Methods for Coupling Alcohols to Solid Supports, Tetrahedron Letters, 35(50) pp. 9333-9336, Dec. 1994.
Fagnola, Maria et al., Solid-Phase Synthesis of Indoles Using the Palladium-Catalysed Coupling of Alkynes with Iodoaniline Derivatives, Tetrahedron Letters 38(13) pp. 2307-2310, Jun. 1997.
Zhang and Maryanoff, "Construction of Indole and Benzofuran Systems of the Solid Phase via Palladium-Mediated Cyclizations," J. Org. Chem. (1997), vol. 62, pp. 1804-1809.
Fagnola, et al., "Solid-Phase Synthesis of Indoles Using the Palladium-Catalysed Coupling of Alkynes with Iodoaniline Derivatives," Tetrahedron Letters, vol. 38, No. 13, (1997), pp. 2307-2310.
Thompson and Ellman, "Straightforward and General Method for Coupling Alcohols to Solid Supports," Tetrahedron Letters, vol. 35, No. 50, (1994), pp. 9333-9336.
Zhang, et al., "Synthesis of Trisubstituted Indoles on the Solid Phase via Palladium-Mediated Heteroannulation of Internal Alkynes," Tetrahedron Letters, vol. 38, No. 14, (1997), pp. 2439-2442.

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