, volume 3 , issue 24 , pages 3827-3830

Solid-Phase Synthesis of 2,3,5-Trisubstituted Indoles

Tom Y.‐H. Wu ¹

Sheng Ding ¹

N. Gray ¹

Peter B. Schultz ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, and Genomics Institute of the Novartis Research Foundation, 3115 Merryfield Row, San Diego, California 92121 |

Publication type: Journal Article

Publication date: 2001-10-31

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/ol016525t

Copy DOI

PubMed ID: 11720546

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

2,3,5-Trisubstituted indoles are synthesized in three steps starting from resin-bound aniline 2. R1 is introduced by a palladium-mediated coupling of the aryl iodide with terminal alkynes followed by intramolecular cyclization to form the indole core. Acylation at C-3 with an acid chloride in the presence of AlCl(3) catalyst introduces R2. The indole C-5 position is then diversified either by Sonagashira or Suzuki couplings with the aryl bromide. Finally, indole N-1 can be modified by post-cleavage methylation. [reaction: see text]

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GOST |

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Wu T. Y. et al. Solid-Phase Synthesis of 2,3,5-Trisubstituted Indoles // Organic Letters. 2001. Vol. 3. No. 24. pp. 3827-3830.

GOST all authors (up to 50) Copy

Wu T. Y., Ding S., Gray N., Schultz P. B. Solid-Phase Synthesis of 2,3,5-Trisubstituted Indoles // Organic Letters. 2001. Vol. 3. No. 24. pp. 3827-3830.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/ol016525t

UR - https://doi.org/10.1021/ol016525t

TI - Solid-Phase Synthesis of 2,3,5-Trisubstituted Indoles

T2 - Organic Letters

AU - Wu, Tom Y.‐H.

AU - Ding, Sheng

AU - Gray, N.

AU - Schultz, Peter B.

PY - 2001

DA - 2001/10/31

PB - American Chemical Society (ACS)

SP - 3827-3830

IS - 24

VL - 3

PMID - 11720546

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2001_Wu,

author = {Tom Y.‐H. Wu and Sheng Ding and N. Gray and Peter B. Schultz},

title = {Solid-Phase Synthesis of 2,3,5-Trisubstituted Indoles},

journal = {Organic Letters},

year = {2001},

volume = {3},

publisher = {American Chemical Society (ACS)},

month = {oct},

url = {https://doi.org/10.1021/ol016525t},

number = {24},

pages = {3827--3830},

doi = {10.1021/ol016525t}

}

MLA

Cite this

MLA Copy

Wu, Tom Y.‐H., et al. “Solid-Phase Synthesis of 2,3,5-Trisubstituted Indoles.” Organic Letters, vol. 3, no. 24, Oct. 2001, pp. 3827-3830. https://doi.org/10.1021/ol016525t.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)