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US 7,078,572 B2Granted
Process for the synthesis of intermediates useful for the synthesis of tubulin inhibitors
AssigneeWyeth Holdings Corporation
InventorJohn Thomas Kendall
Life of this patent
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Abstract
The invention is a process for the preparation of compounds of the Formula I: where R1, R2, R3, R4 and R5 are defined in the specification, which are intermediates useful for the preparation of tubulin inhibitors which are useful in the treatment of cancer.
Claims7
A process for the preparation of an aldehyde of the formula:
- wherein:
- R1 and R2 are independently selected from H, straight chain alkyl of 1 to 4 carbon atoms, halogen and alkoxy of 1 to 4 carbon atoms;
- R3 is straight chain alkyl of 1 to 4 carbon atoms;
- by reacting a substituted oxirane of the formula:
- with tris(pentafluorophenyl) borane to afford an aldehyde of the formula
2 more elements
A process for the preparation of an aldehyde of the formula:
- wherein:
- R1 and R2 are independently selected from H, straight chain alkyl of 1 to 4 carbon atoms, halogen and alkoxy of 1 to 4 carbon atoms;
- R3 is straight chain alkyl of 1 to 4 carbon atoms;
- R4 is straight chain alkyl of 1 to 4 carbon atoms and branched chain alkyl of 3 to 4 carbon atoms;
- R5 is straight chain alkyl of 1 to 4 carbon atoms;
- comprising
- a) alkylating benzylnitrile of the formula:
- with an alkylating agent R3LG, in the presence of a strong base, to obtain a nitrile of the formula:
- and
- b) reducing a nitrile of step a with a reducing agent to give an aldehyde of the formula:
7 more elements
Dependencies are inferred from the claim text.