Development of a pilot-plant process for a nevirapine analogue HIVNNRT inhibitor

被引：21

作者：

Busacca, Carl A. ^{[1
]}

Cerreta, Mike ^{[1
]}

Dong, Yong ^{[1
]}

Eriksson, Magnus C. ^{[1
]}

Farina, Vittorio ^{[1
]}

Feng, XuWu ^{[1
]}

Kim, Ji-Young ^{[1
]}

Lorenz, Jon C. ^{[1
]}

Sarvestani, Max ^{[1
]}

Simpson, Robert ^{[1
]}

Varsolona, Rich ^{[1
]}

Vitous, Jana ^{[1
]}

Campbell, Scot J. ^{[2
]}

Davis, Mark S. ^{[2
]}

Jones, Paul-James ^{[2
]}

Norwood, Daniel ^{[2
]}

Qiu, Fenghe ^{[2
]}

Beaulieu, Pierre L. ^{[3
]}

Duceppe, Jean-Simon ^{[3
]}

Hache, Bruno ^{[3
]}

Brong, Jim ^{[4
]}

Chiu, Fang-Ting ^{[4
]}

Curtis, Tom ^{[4
]}

Kelley, Jason ^{[4
]}

Lo, Young S. ^{[4
]}

Powner, Tory H. ^{[4
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Analyt Sci, Ridgefield, CT 06877 USA

[2] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA

[3] Boehringer Ingelheim Canada Ltd, Laval, PQ H7S 2GS, Canada

[4] Boehringer Ingelheim Chem Inc, Petersburg, VA 23805 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2008年 / 12卷 / 04期

关键词：

D O I：

10.1021/op8000756

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The pilot-plant synthesis of nevirapine analogue (1) under bar is described. The compound was prepared in eight steps from substituted pyridine raw materials and 4-hydroxyquinoline. The key transformation involves a novel one-pot conversion of an arylhalide to arylacetic acid under palladium catalysis, followed by regioselective reduction via in situ generated BH3/THF to the arylethanol intermediate 2. All stages were carried out on 10-150-kg scale.

引用

页码：603 / 613

页数：11

共 39 条

[1] AN IMPROVED, CONVENIENT PROCEDURE FOR REDUCTION OF AMINO-ACIDS TO AMINOALCOHOLS - USE OF NABH4-H2SO4 [J].

ABIKO, A ;

MASAMUNE, S .

TETRAHEDRON LETTERS, 1992, 33 (38) :5517-5518

[2] Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands [J].

Beare, NA ;

Hartwig, JF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :541-555

[3]

BEAULIEU PL, 2002, SYNTHESIS-STUTTGART, V4, P528

[4] RECENT PROGRESS IN THE CONTROL OF CARBON VERSUS OXYGEN ACYLATION OF ENOLATE ANIONS [J].

BLACK, TH .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1989, 21 (02) :179-&

[5] THE PHENYLDIMETHYLSILYL GROUP AS A MASKED FORM OF THE HYDROXY GROUP [J].

FLEMING, I ;

HENNING, R ;

PLAUT, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (01) :29-31

[6] THE PHENYLDIMETHYLSILYL GROUP AS A MASKED HYDROXY GROUP [J].

FLEMING, I ;

HENNING, R ;

PARKER, DC ;

PLAUT, HE ;

SANDERSON, PEJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (04) :317-337

[7] Highly active and selective catalysts for the formation of α-aryl ketones [J].

Fox, JM ;

Huang, XH ;

Chieffi, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370

[8] Synthesis of five nevirapine metabolites [J].

Grozinger, KG ;

Byrne, DP ;

Nummy, LJ ;

Ridges, MD ;

Salvagno, A .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (02) :229-239

[9] PHOTOCHEMICAL MAGNETIC-FIELD EFFECTS OF ISOQUINOLINE N-OXIDE IN VARIOUS ALCOHOLS [J].

HATA, N .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (09) :2723-2728

[10] RADICAL ION-PAIR MECHANISM OF THE PHOTOCHEMICAL ISOMERIZATION OF ISOQUINOLINE N-OXIDE IN HYDROXYLIC SOLVENTS, INCLUDING THE MAGNETIC-FIELD EFFECT [J].

HATA, N ;

YAGI, A .

CHEMISTRY LETTERS, 1983, (03) :309-312

← 1 2 3 4 →