pylioja's blog

02 Nov

A range of compounds are ready for testing with more coming.

Published by pylioja

Subject 

Request for Help

I'm now happy with the data for TCMDC-123812 and TCMDC-123794. A bit of usual practical annoynce with TCMDC-123794 caused some trivial issues, namely a bit of repurification and acetone in the final spectra. These have now been taken care of and the compounds are ready for testing!

09 Oct

TCMDC-123812 and 123794, pending purification.

Published by pylioja

Subject 

Request for Help

I'm now fairly confident that I've made TCMDC-123794 and TCMDC-123812. By fairly confident I mean that I've got a reasonable looking but crude 1H NMR and low res. mass spec of both of the compounds. They are not clean by NMR after a column and the yield of the reaction was pretty bad (~20%). Still this isn't too bad for a first go, using a quick and dirty acid chloride. Most of the mass seems to go toward turning the acid into the anhydride.

21 Sep

Now we're getting somewhere but not with the oxidation

Published by pylioja

Subject 

Miscellaneous

Ok now I'm getting close to TCMDC-123812/123794. A slight change of tack for the alternative core synthesis seems to have paid off. First alkylation of ethyl acetoacetate with chloroacetone and then condensation with 4-fluoroaniline appears to have given the pyrrole with an ester on the 3-position quite nicely in 61% yield over the two steps after recrystallisation (PMY 8-1). Sometimes it just pays to change the plan completely when you feel like progress is slow.

19 Sep

Update on TCMDC-123812 and TCMDC-123794: Oxidation issues

Published by pylioja

Subject 

Rants

In the last couple of weeks my time has mostly been spent trying to figure out whats going on in the oxidation of pyrrole-3-carbaldehyde to the corresponding acid.
Reaction Scheme PY3_5.png

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