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7th January 2014 @ 08:18

The OSM team are currently trying to synthesise some triazalopyrazines (series 4) that were found to be promising antimalarial starting points by big pharma.

I (Alice in Mat Todd's group at the University of Sydney) am currently attempting to resynthesise MMV670652 in order to confirm the activity of the racemate and subsequently determine the activity of each enantiomer following resolution.

I have been following a procedure provided by the CRO who had worked on these compounds. The CRO used Freon gas to difluoromethylate AEW 103 and unfortunately, due to limitations on the availability of Freon-22 in Australia, the team need to find an alternative method for this transformation:

The methods I have attempted so far involved the use of the diflurocarbene generating reagent trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate.

I'm going to try some more conditions and also the use of the more toxic 2,2-difluoro-2-(fluorosulfonyl)acetic acid but would be most grateful for any ideas or assistance in how to get this reaction to work.

Attached Files
OSM BLOG_difluoromethylation.png
OSM blog dif.png
OSM blog dif2.png