An efficient synthesis of the indole acetic acid metabolite of MK-0462

被引：15

作者：

Chen, CY ^{[1
]}

Lieberman, DR ^{[1
]}

Street, LJ ^{[1
]}

Guiblin, AR ^{[1
]}

Larsen, RD ^{[1
]}

Verhoeven, TR ^{[1
]}

机构：

[1] MERCK SHARP & DOHME LTD, RES LABS, HARLOW CM20 2QR, ESSEX, ENGLAND

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 10期

关键词：

D O I：

10.1080/00397919608003552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed coupling of iodoaniline 2 with bis-TES propargyl alcohol 3 gives indole-3-methanol 4b in 72% yield. Displacement of the hydroxy group of 4b by sodium cyanide followed by hydrolysis of the cyano group and desilylation provides the indole acetic acid metabolite, L-749,335 (1), of the 5-HT1D receptor agonist MK-0462.

引用

页码：1977 / 1984

页数：8

共 10 条

[1] IMPROVED FISCHER INDOLE REACTION FOR THE PREPARATION OF N,N-DIMETHYLTRYPTAMINES - SYNTHESIS OF L-695,894, A POTENT 5-HT1D RECEPTOR AGONIST [J].

CHEN, CY ;

SENANAYAKE, CH ;

BILL, TJ ;

LARSEN, RD ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3738-3741

[2] SYNTHESIS OF THE 5-HT1D RECEPTOR AGONIST MK-0462 VIA A PD-CATALYZED COUPLING REACTION [J].

CHEN, CY ;

LIEBERMAN, DR ;

LARSEN, RD ;

REAMER, RA ;

VERHOEVEN, TR ;

REIDER, PJ ;

COTTRELL, IF ;

HOUGHTON, PG .

TETRAHEDRON LETTERS, 1994, 35 (38) :6981-6984

[3] CYANOMETHYLATION OF INDOLE [J].

COKER, JN ;

MATHRE, OB ;

TODD, WH .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :589-&

[4] A CONVENIENT METHOD FOR THE SYNTHESIS OF INDOLE-3-ACETIC ACIDS [J].

GUAN, XM ;

BORCHARDT, RT .

TETRAHEDRON LETTERS, 1994, 35 (19) :3013-3016

[5] SYNTHESIS OF INDOLES VIA PALLADIUM-CATALYZED HETEROANNULATION OF INTERNAL ALKYNES [J].

LAROCK, RC ;

YUM, EK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6689-6690

[6]

LIU L, 1994, AM ASS PHARM SCI 9 A

[7]

RUNTI C, 1953, ANN CHIM-ROME, V43, P308

[8]

SPANDE TF, CHEM HETEROCYCLIC 3, V25, P1

[9] SYNTHESIS AND SEROTONERGIC ACTIVITY OF N,N-DIMETHYL-2-[5-(1,2,4-TRIAZOL-1-YLMETHYL)-1H-INDOL-3-YL] ETHYLAMINE AND ANALOGS - POTENT AGONISTS FOR 5-HT1D RECEPTORS [J].

STREET, LJ ;

BAKER, R ;

DAVEY, WB ;

GUIBLIN, AR ;

JELLEY, RA ;

REEVE, AJ ;

ROUTLEDGE, H ;

STERNFELD, F ;

WATT, AP ;

BEER, MS ;

MIDDLEMISS, DN ;

NOBLE, AJ ;

STANTON, JA ;

SCHOLEY, K ;

HARGREAVES, RJ ;

SOHAL, B ;

GRAHAM, MI ;

MATASSA, VG .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (10) :1799-1810

[10] TANDEM MICHAEL ADDITION [3,3]SIGMATROPIC REARRANGEMENT PROCESSES .2. CONSTRUCTION OF CYCLOPROPA[3,4]PYRROLO[3,2-E]INDOL-4-ONE (CPI) UNIT OF ANTITUMOR ANTIBIOTIC CC-1065 [J].

TOYOTA, M ;

FUKUMOTO, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :547-552

← 1 →