Practical synthesis of 3-carboxyindazoles

被引：3

作者：

Johnson, BL ^{[1
]}

Rodgers, JD ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Wallingford, CT 06492 USA

来源：

SYNTHETIC COMMUNICATIONS | 2005年 / 35卷 / 20期

关键词：

carboxyindazole; indazole; indazole carboxylic acid; indazolone;

D O I：

10.1080/00397910500214318

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A clean, high-yielding synthetic route to methyl 5-(bromomethyl)-1-tritylindazole 3-carboxylate 1 was needed. A principal intermediate was 5-methyl-3-carboxyindazole 2. An analysis of a by-product found after executing Schad's 3-carboxyindazole synthesis led to undertaking this reaction with an inverse addition in the principal step. This simple modification gave 2 in excellent and reproducible yields.

引用

页码：2681 / 2684

页数：4

共 12 条

[1]

BAIOCCHI L, 1978, SYNTHESIS-STUTTGART, P633

[2] THE SEROTONIN 5-HT4 RECEPTOR .2. STRUCTURE-ACTIVITY STUDIES OF THE INDOLE CARBAZIMIDAMIDE CLASS OF AGONISTS [J].

BUCHHEIT, KH ;

GAMSE, R ;

GIGER, R ;

HOYER, D ;

KLEIN, F ;

KLOPPNER, E ;

PFANNKUCHE, HJ ;

MATTES, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (13) :2331-2338

[3] INDAZOLE-3-CARBOXYLIC ACIDS AND THEIR DERIVATIVES [J].

BUUHOI, NP ;

HOEFFINGER, JP ;

JACQUIGNON, P .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1964, 1 (05) :239-+

[4] INDAZOLES AS INDOLE BIOISOSTERES - SYNTHESIS AND EVALUATION OF THE TROPANYL ESTER AND AMIDE OF INDAZOLE-3-CARBOXYLATE AS ANTAGONISTS AT THE SEROTONIN 5HT3 RECEPTOR [J].

FLUDZINSKI, P ;

EVRARD, DA ;

BLOOMQUIST, WE ;

LACEFIELD, WB ;

PFEIFER, W ;

JONES, ND ;

DEETER, JB ;

COHEN, ML .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) :1535-1537

[5]

HARADA H, 1995, CHEM PHARM BULL, V43, P1912

[6]

RODGERS JD, 1997, 3K NAT ORG CHEM S SA, pM108

[7]

RODGERS JD, 1997, 16 INT C HET CHEM BO

[8]

SCHAD P, 1893, CHEM BER, V26, P216

[9] THE SYNTHESIS OF AN INDAZOLE ANALOG OF DL-TRYPTOPHAN [J].

SNYDER, HR ;

THOMPSON, CB ;

HINMAN, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (08) :2009-2012

[10]

VONAUWERS K, 1919, CHEM BER, V52, P1340

← 1 2 →