Preparation of ethyl 5-iodo-1H-indole-2-carboxylate

被引：7

作者：

Beshore, DC ^{[1
]}

Dinsmore, CJ ^{[1
]}

机构：

[1] Merck Res Labs, Dept Med Chem, W Point, PA 19486 USA

来源：

SYNTHETIC COMMUNICATIONS | 2003年 / 33卷 / 14期

关键词：

indole; regioselective halogenation; dehalogenation;

D O I：

10.1081/SCC-120021830

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile, two step procedure for the preparation of ethyl 5-iodo-1H-indole-2-carboxylate (1) from commercially available ethyl 1H-indole-2-carboxylate is described herein, employing a regioselective C3, C5-bisiodination followed by zinc-mediated C3-dehalogenation.

引用

页码：2423 / 2427

页数：5

共 14 条

[1] Metal-mediated reductive hydrodehalogenation of organic halides
Alonso, F
Beletskaya, IP
Yus, M
[J]. CHEMICAL REVIEWS, 2002, 102 (11) : 4009 - 4091
[2] CHEMISTRY OF INDOLO[1,2-C]QUINAZOLINE - AN APPROACH TO THE MARINE ALKALOID HINCKDENTINE-A
BILLIMORIA, AD
CAVA, MP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) : 6777 - 6782
[3] Synthesis and isolation of iodocarbazoles.: Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system
Bonesi, SM
Erra-Balsells, R
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (01) : 77 - 87
[4] On the synthesis and isolation of chlorocarbazoles obtained by chlorination of N-substituted carbazoles
Bonesi, SM
ErraBalsells, R
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (03) : 891 - 900
[5] On the synthesis and isolation of chlorocarbazoles obtained by chlorination of carbazoles
Bonesi, SM
ErraBalsells, R
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (03) : 877 - 889
[6] MECHANISM OF AROMATIC IODINATION
BUTLER, AR
[J]. JOURNAL OF CHEMICAL EDUCATION, 1971, 48 (08) : 508 - &
[7] A facile debromination reaction: Can bromide now be used as a protective group in aromatic systems?
Choi, HY
Chi, DY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) : 9202 - 9203
[8] PROTONATION OF INDOLES - POSITION OF PROTONATION
HINMAN, RL
WHIPPLE, EB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (13) : 2534 - &
[9] Joule J. A., 2000, HETEROCYCLIC CHEM, P319
[10] Iodination of both deactivated and activated arenes with sodium periodate or sodium iodate as the oxidants
Lulinski, P
Skulski, L
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (04) : 951 - 956

← 1 2 →