Process for preparing 1,4-dibenzodiazepines via Buchwald-Hartwig chemistry
AssigneeUniversidade De Evora
InventorsAnthony Burke, Daniela Alexandra Silva Peixoto
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Abstract
The present application provides a one-pot catalytic process which involves the formation of 1,4-dibenzodiazepines from o-haloaldimines (either pre-formed or formed in situ) of formula (I) and o-haloanilines of formula (II) via a palladium catalyzed Buchwald-Hartwig reaction and a cyclization sequence, to afford the 1,4-dibenzodiazepine products of formula (III). The present application describes the preparation of the 1,4-dibenzodiazepine products of formula (III) from simple commercial raw materials by efficient processes.
Claims10
A process for the catalytic one-pot synthesis of products of formula (III) from substrates of formula (I) and (II) respectively,
- wherein,
- X represents a halogen group or a triflate group (OTf);
- R represents, an alkyl or aryl group;
- R1 and R3 represent a hydrogen, a saturated alkyl, allyl, vinyl or cycloalkyl group, or an aryl group, or an OH, tiol, amino, nitro, cyano, aldehyde, ketone, ester, thioester, carboxylic acid, carbamate, ether or a thioeter group;
- R2 represents a hydrogen, an alkyl, allyl, vinyl or aryl group;
- comprising the use of an active palladium catalyst, at a loading of between 0.1 and 5 mol %, wherein the reaction is
- conducted by adding a palladium complex, a ligand at a loading of between 0.25 and 10 mol %, and a base in a solvent.
Dependencies are inferred from the claim text.