Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium

Takao Sakamoto; Eisaku Katoh; Yoshinori Kondo; Hiroshi Yamanaka

doi:10.1248/cpb.36.1664

Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium

Takao Sakamoto, Eisaku Katoh, Yoshinori Kondo, Hiroshi Yamanaka

PHA - Molecular Pharmaceutical Science

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

32 Citations (Scopus)

Abstract

The cross-coupling of 3-iodo- and 3-bromopyridine with the carbanions derived from ethyl cyanoacetate and malononitrile in the presence of tetrakis(triphenylphosphine)palladium in 1,2-dimethoxyethane gave ethyl α-cyanopyridine-3-acetate and 3-pyridinemalononitrile in moderate yields. This palladium-catalyzed cross-coupling proceeded smoothly with halopyrimidines, halo-quinolines, haloisoquinolines, and also bromobenzene.

Original language	English
Pages (from-to)	1664-1668
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	36
Issue number	5
DOIs	https://doi.org/10.1248/cpb.36.1664
Publication status	Published - 1988

Keywords

N-heteroaryl halide
arenemalononitrile
aryl halide
ethyl cyanoacetate
ethyl α-cyanoareneacetate
malononitrile
tetrakis(triphenylphosphine)palladium

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.36.1664

Cite this

@article{dc0e900c6fee4e35ac26dcc2c032cac5,

title = "Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium",

abstract = "The cross-coupling of 3-iodo- and 3-bromopyridine with the carbanions derived from ethyl cyanoacetate and malononitrile in the presence of tetrakis(triphenylphosphine)palladium in 1,2-dimethoxyethane gave ethyl α-cyanopyridine-3-acetate and 3-pyridinemalononitrile in moderate yields. This palladium-catalyzed cross-coupling proceeded smoothly with halopyrimidines, halo-quinolines, haloisoquinolines, and also bromobenzene.",

keywords = "N-heteroaryl halide, arenemalononitrile, aryl halide, ethyl cyanoacetate, ethyl α-cyanoareneacetate, malononitrile, tetrakis(triphenylphosphine)palladium",

author = "Takao Sakamoto and Eisaku Katoh and Yoshinori Kondo and Hiroshi Yamanaka",

year = "1988",

doi = "10.1248/cpb.36.1664",

language = "English",

volume = "36",

pages = "1664--1668",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "5",

}

TY - JOUR

T1 - Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium

AU - Sakamoto, Takao

AU - Katoh, Eisaku

AU - Kondo, Yoshinori

AU - Yamanaka, Hiroshi

PY - 1988

Y1 - 1988

N2 - The cross-coupling of 3-iodo- and 3-bromopyridine with the carbanions derived from ethyl cyanoacetate and malononitrile in the presence of tetrakis(triphenylphosphine)palladium in 1,2-dimethoxyethane gave ethyl α-cyanopyridine-3-acetate and 3-pyridinemalononitrile in moderate yields. This palladium-catalyzed cross-coupling proceeded smoothly with halopyrimidines, halo-quinolines, haloisoquinolines, and also bromobenzene.

AB - The cross-coupling of 3-iodo- and 3-bromopyridine with the carbanions derived from ethyl cyanoacetate and malononitrile in the presence of tetrakis(triphenylphosphine)palladium in 1,2-dimethoxyethane gave ethyl α-cyanopyridine-3-acetate and 3-pyridinemalononitrile in moderate yields. This palladium-catalyzed cross-coupling proceeded smoothly with halopyrimidines, halo-quinolines, haloisoquinolines, and also bromobenzene.

KW - N-heteroaryl halide

KW - arenemalononitrile

KW - aryl halide

KW - ethyl cyanoacetate

KW - ethyl α-cyanoareneacetate

KW - malononitrile

KW - tetrakis(triphenylphosphine)palladium

UR - http://www.scopus.com/inward/record.url?scp=58149155215&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=58149155215&partnerID=8YFLogxK

U2 - 10.1248/cpb.36.1664

DO - 10.1248/cpb.36.1664

M3 - Article

AN - SCOPUS:58149155215

VL - 36

SP - 1664

EP - 1668

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 5

ER -

Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this