Eli Lilly and Company

University of East Anglia

Other

Princeton University

Interox Chemicals Limited

Alexander McKillop

Jason Scott Sawyer

Nicholas J Bach

Stephen Richard Baker

Jeremy Gilmore

Russell Andrew Lewthwaite

George Richard Stephenson

Michael William Urquhart

Michael William John Urquhart

Duncan Kemp

This invention relates to a method of making N-benzyl indoles, and to intermediates for use in the method, and to certain substantially optically pure N-benzyl indoles obtained by the method.

Process for preparing N-benzyl indoles

Process for preparing n-benzyl indoles

A process for producing a compound of the formu5la ##STR1## comprising the step of reacting a compound of the formula ##STR2## with a compound of the formula ##STR3## to form a compound of the formula ##STR4## wherein R.sup.2a is selected from the groups recited above for R.sup.2, or R.sup.2a --X-- is a protected hydroxyl group, and Z is a group of formula --Y--R.sub.5 recited above, or a group that can be converted into a group of said formula --Y--R.sup.5. Intermediates of formula IV and composition containing substantially optically pure enantiomers of Formula (I) are included within the scope of the invention.

Substituted anilino-nicotinic acid derivatives are readily prepared from the condensation of two intermediates, 2-alkyl-3-perfluoroalkyl-anilines and alkyl 2-chloronicotinates. The 2-alkyl-3-perfluoroalkyl-aniline intermediate can be prepared via a novel three step synthesis. 3-Perfluoroalkyl-anilines are reacted with an amine directing protecting group reagent to protect the amine. The protected amine is then alkylated, and finally, the directing group is removed to form the 2-alkyl-3-perfluoroalkyl-aniline intermediate. The 2-alkyl-3-perfluoroalkyl-aniline intermediate is condensed with the alkyl 2-chloronicotinate to form the anilino-nicotinic acid derivative.

Preparation of substituted anilino-nicotinic acid derivatives

Process for preparing iodoarene compounds

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Norwich, United Kingdom

Alexander McKillop