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Newsletter Issue 57 Jan 2016

Scientific Updates' What's New in Process ChemistryScientific Update
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Amide Formation


Dr Will Watson

Two novel ways to form amides have been published recently:

1. The Boc group is probably the most commonly used amine protecting group particularly in fine chemical and pharmaceutical process development, and amide formation is one of the most common transformations, and now you can convert you Boc protected amine to an amide directly in a Rh catalysed reaction with a boronate:

Scheme1

Cyclopropanation


Dr Will Watson

Cyclopropanation of olefins, particularly styrenes, usually requires the use of metal catalysts (typically Rh) and hazardous reagents such as ethyl diazoacetate, however 2 recent papers describe metal free cyclopropanation methods that do not require hazardous reagents and work under mild conditions. The key is the use of light as an alternative reagent.

Scheme3

ortho-Alkylation of Nitroheterocycles


Dr Will Watson

Making poly-substituted indoles and related heterocycles can still be a challenge, but this paper from AstraZeneca provides an interesting way to make alkylated nitroindoles and carbazoles as well as benzothiophenes and benzofurans.

Scheme6

Genotoxic Impurities


Dr Will Watson

Those of you working with or in the pharmaceutical industry will no doubt be familiar with the topic of Genotoxic Impurities, and you are probably aware that there was a special feature in the November 2015 issue of Organic Process Research and Development on Genotoxic Impurities (11 papers). What you may have missed is a review entitled “Genotoxic Impurities in Pharmaceutical Manufacturing: Sources, Regulations, and Mitigation” that was published in issue 16 (August 26) of Chemical Reviews last year (2015).

G. Szekely,* M.C. Amores de Souza, M. Gil, F.C. Ferreira, and W. Heggie,* Chem. Rev., 2015, 115, 8182-8229.

Direct Cross Coupling of Phenols with Amines


Dr Will Watson

Buchwald-Hartwig cross-couplings are frequently used to make anilines but they typically require a halide or pseudo-halide starting material. This paper describes a formal direct amination of phenols.

Scheme8

An Alternative Hydrazine for the Wolff-Kishner Reduction


Dr Will Watson

The Wolff-Kishner Reduction remains a very useful method for reducing ketones and aldehydes to CH2 or CH3 respectively, and in some cases it is the only viable option,1 but the use of hydrazine is drawback from a safety perspective. Now we have an alternative – methyl hydrazinocarboxylate, NH2NHCO2Me. The method presented in this paper2 does involve making the hydrazone as a separate operation and an equivalent of CO2 gas is formed as well as N2, but yields are respectable.

Scheme10.gif

And Finally


Dr Will Watson

You frequently see new catalyst systems being published for carrying out reactions such as the Suzuki-Maiyaura cross coupling reaction, but I challenge anyone to come with a more bizarre catalyst system than the one described in this paper entitled “Sustainable Catalysis using magnetic chicken feathers decorated with Pd(0) for Suzuki-cross coupling reaction”.
And no it was not published on April 1st!

And just in case you doubt this I have quoted the first line of the Abstract:

“Magnetic nano-particles (Fe3O4) coated with chicken feather (CF) were synthesized and subsequently grafted with palladium nanoparticles (Pd NPs) using in situ approach.”

P.P Lathma, M. Bhatt, and S.L. Jain, Tet. Letts., 2015, 56, 5718-5722.

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