An efficient one-pot synthesis of novel 4-aryl-1-methyloxindoles

Adri van den Hoogenband; Jos H.M. Lange; Wouter I. Iwema-Bakker; Jack A.J. den Hartog; Jord van Schaik; Rolf W. Feenstra; Jan Willem Terpstra

doi:10.1016/j.tetlet.2006.04.103

An efficient one-pot synthesis of novel 4-aryl-1-methyloxindoles

Adri van den Hoogenband
, Jos H.M. Lange
, Wouter I. Iwema-Bakker
, Jack A.J. den Hartog
, Jord van Schaik
, Rolf W. Feenstra
, Jan Willem Terpstra

Solvay Pharmaceuticals

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

An unprecedented synthetic approach to novel 4-aryl-1-methyloxindoles is described. The method involves the intramolecular palladium-catalyzed amidation of N-methyl-2,6-dibromophenylacetamide followed by an in situ Suzuki cross-coupling reaction with a (hetero)arylboronic acid in a one-pot reaction. © 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4361-4364
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2006.04.103
Publication status	Published - 26 Jun 2006
Externally published	Yes

Keywords

1 methyloxindole derivative
4 methoxyphenylboronic acid
acetamide derivative
benzeneboronic acid
boronic acid derivative
furan 2 boronic acid
indole derivative
n methyl 2,6 dibromophenylacetamide
palladium
thiophene 2 boronic acid
unclassified drug
amidation
article
bromination
catalysis
Suzuki reaction
synthesis

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10.1016/j.tetlet.2006.04.103

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title = "An efficient one-pot synthesis of novel 4-aryl-1-methyloxindoles",

abstract = "An unprecedented synthetic approach to novel 4-aryl-1-methyloxindoles is described. The method involves the intramolecular palladium-catalyzed amidation of N-methyl-2,6-dibromophenylacetamide followed by an in situ Suzuki cross-coupling reaction with a (hetero)arylboronic acid in a one-pot reaction. {\textcopyright} 2006 Elsevier Ltd. All rights reserved.",

keywords = "1 methyloxindole derivative, 4 methoxyphenylboronic acid, acetamide derivative, benzeneboronic acid, boronic acid derivative, furan 2 boronic acid, indole derivative, n methyl 2,6 dibromophenylacetamide, palladium, thiophene 2 boronic acid, unclassified drug, amidation, article, bromination, catalysis, Suzuki reaction, synthesis",

author = "\{van den Hoogenband\}, Adri and Lange, \{Jos H.M.\} and Iwema-Bakker, \{Wouter I.\} and \{den Hartog\}, \{Jack A.J.\} and \{van Schaik\}, Jord and Feenstra, \{Rolf W.\} and Terpstra, \{Jan Willem\}",

year = "2006",

month = jun,

day = "26",

doi = "10.1016/j.tetlet.2006.04.103",

language = "English",

volume = "47",

pages = "4361--4364",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "26",

}

TY - JOUR

T1 - An efficient one-pot synthesis of novel 4-aryl-1-methyloxindoles

AU - van den Hoogenband, Adri

AU - Lange, Jos H.M.

AU - Iwema-Bakker, Wouter I.

AU - den Hartog, Jack A.J.

AU - van Schaik, Jord

AU - Feenstra, Rolf W.

AU - Terpstra, Jan Willem

PY - 2006/6/26

Y1 - 2006/6/26

N2 - An unprecedented synthetic approach to novel 4-aryl-1-methyloxindoles is described. The method involves the intramolecular palladium-catalyzed amidation of N-methyl-2,6-dibromophenylacetamide followed by an in situ Suzuki cross-coupling reaction with a (hetero)arylboronic acid in a one-pot reaction. © 2006 Elsevier Ltd. All rights reserved.

AB - An unprecedented synthetic approach to novel 4-aryl-1-methyloxindoles is described. The method involves the intramolecular palladium-catalyzed amidation of N-methyl-2,6-dibromophenylacetamide followed by an in situ Suzuki cross-coupling reaction with a (hetero)arylboronic acid in a one-pot reaction. © 2006 Elsevier Ltd. All rights reserved.

KW - 1 methyloxindole derivative

KW - 4 methoxyphenylboronic acid

KW - acetamide derivative

KW - benzeneboronic acid

KW - boronic acid derivative

KW - furan 2 boronic acid

KW - indole derivative

KW - n methyl 2,6 dibromophenylacetamide

KW - palladium

KW - thiophene 2 boronic acid

KW - unclassified drug

KW - amidation

KW - article

KW - bromination

KW - catalysis

KW - Suzuki reaction

KW - synthesis

U2 - 10.1016/j.tetlet.2006.04.103

DO - 10.1016/j.tetlet.2006.04.103

M3 - Article

SN - 0040-4039

VL - 47

SP - 4361

EP - 4364

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

An efficient one-pot synthesis of novel 4-aryl-1-methyloxindoles

Abstract

Keywords

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