An improved synthesis of a novel α1A partial agonist including a new two-step synthesis of 4-fluoropyrazole

被引：6

作者：

England, Katherine ^{[1
]}

Mason, Helen ^{[1
]}

Osborne, Rachel ^{[1
]}

Roberts, Lee ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Worldwide Med Chem, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 21期

关键词：

HETEROCYCLIC-COMPOUNDS; ROUTE;

D O I：

10.1016/j.tetlet.2010.03.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This Letter outlines a new two-step process for the synthesis of 4-fluoropyrazole and its application in an improved synthesis of 4-fluoro-1-[5-fluoro-1-(1H-imidazol-2-yl)-indan-4-ylmethyl]-1H-pyrazole. The original synthesis of 4-fluoro-1-[5-fluoro-1-(1H-imidazol-2-y1)-indan-4-ylmethyl]-1H-pyrazole is also described. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2849 / 2851

页数：3

共 9 条

[1] Palladium catalyzed cross-coupling reaction of 5-tributylstannyl-4-fluoropyrazole [J].

Hanamoto, T ;

Koga, Y ;

Kido, E ;

Kawanami, T ;

Furuno, H ;

Inanagah, J .

CHEMICAL COMMUNICATIONS, 2005, (15) :2041-2043

[2] N-arylation of 4-fluoro-5-trimethylsilyl-1H-pyrazole [J].

Hanamoto, Takeshi ;

Iwamoto, Yuhko ;

Yamada, Kenji ;

Anno, Ryoko .

JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (10) :1126-1130

[3] Direct synthesis of 3-arylpropionic acids by tetraphosphine/palladium catalysed Heck reactions of aryl halides with acrolein ethylene acetal [J].

Lemhadri, M ;

Doucet, H ;

Santelli, M .

TETRAHEDRON, 2004, 60 (50) :11533-11540

[4] FLUOROMALONALDEHYDE BIS(DIALKYL ACETALS) - SYNTHESIS BY CARBENE CONDENSATION AND TRANSFORMATION TO DIALKYL FLUOROMALONATES AND FLUORINATED HETEROCYCLIC-COMPOUNDS [J].

MOLINES, H ;

WAKSELMAN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) :5618-5620

[5]

REICHARDT C, 1970, LIEBIGS ANN CHEM, P99

[6]

REICHARDT C, 1975, LIEBIGS ANN CHEM, P470

[7] Novel 2-imidazoles as potent, selective and CNS penetrant α1A adrenoceptor partial agonists [J].

Roberts, Lee R. ;

Bryans, Justin ;

Conlon, Kelly ;

McMurray, Gordon ;

Stobie, Alan ;

Whitlock, Gavin A. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (24) :6437-6440

[8] REACTIONS OF BETA-FLUOROVINAMIDINIUM SALT WITH BIFUNCTIONAL HETERO NUCLEOPHILES - A NEW SYNTHETIC ROUTE TO FLUORINATED HETEROCYCLES [J].

SHI, XF ;

ISHIHARA, T ;

YAMANAKA, H ;

GUPTON, JT .

TETRAHEDRON LETTERS, 1995, 36 (09) :1527-1530

[9] RHODIUM COMPLEX-CATALYZED DESILYLATIVE CYCLOCARBONYLATION OF 1-ARYL-2-(TRIMETHYLSILYL)ACETYLENES - A NEW ROUTE TO 2,3-DIHYDRO-1H-INDEN-1-ONES [J].

TAKEUCHI, R ;

YASUE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5386-5392

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