Development and application of automation-friendly catalytic reductions of NBn, OBn, NCBz and NO₂ groups to parallel synthesis

ORGN 552

Lixin Shen, Chris Lanthier, Fushuang Liu, Audra Dalton, George Kosturko, Libing Yu, and Carmen Baldino. Chemistry Department, ArQule, Inc, 19 Presidential Way, Woburn, MA 01801

In our effort to adapt existing transformations to parallel synthesis, we have developed an automation-friendly catalytic reduction method. Pd/Al2O3 coupled with a reducing reagent such as NH4CO2H or Et3SiH, was effectively used to reduce NBn, OBn, NCBz and NO2 groups in library format. Furthermore, this method has been utilized successfully in parallel synthesis of a library of analogs of 1, an inhibitor of metalloproteinases, and a focused library of analogs related to the antitumor agent 2.

Combinatorial, parallel, and solid-phase chemistry 1:00 PM-5:00 PM, Wednesday, March 31, 2004 Anaheim Convention Center -- 303A, Oral Division of Organic Chemistry The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004