The Lab Notes

Figure 1: Suzuki-Miyaura Coupling   It’s a reaction that most organic chemists have run at some stage in their careers and is almost certainly in the running for the most widely used C-C bond forming reaction. First reported in 1979, the Suzuki-Miyaura cross-coupling between an organoboron nucleophile and an aryl halide electrophile is still ubiquitous in…

Vanadium (V, Element 23) Vanadium, a group 5 transition metal, discovered in 1801 by Andres Manuel del Rio, occurs naturally as a component of vanadinite (Pb5(VO4)3Cl), one of the main industrial ores used as a source of the metal. Over 60 ores are known, with 70-80 thousand tonnes of ore mined globally each year, producing…

Heterocyclic phosphonium salts- powerful intermediates for pyridine coupling:- I’ve always had a keen interest in phosphorus chemistry and have followed the work of the McNally group at Colorado state on heterocyclic phosphonium salts closely. In late 2016 a paper describing synthesis and application of the so called HetPhos salts for C4 (or C2) functionalisation of…

Figure 1 I guess to qualify as a reagent of the month the material has to fulfil certain criteria and commercial availability, though not essential, is very desirable. N-((Methylsulfonyl)oxy)acetimiodyl chloride (henceforth known, at least by me, as Fier’s reagent) is now available to buy from Sigma Aldrich (CAS: 1433887-06-9). The compound is an air and…

Gin is rapidly becoming the nations favourite tipple. Its undergone a modern renaissance with familiar trade names such as Gordon’s, Plymouth and London and multiple artisan distilleries appearing country-wide. It’s even drawn synthetic organic chemists out of the lab and into the refineries. This week at our 5th Winter Process Chemistry Conference in Manchester UK…

Figure: 1 The idea of using transition metal chemistry in a cellular setting might at first seem counterintuitive- biological conditions are challenging with respect to stability, efficiency and catalyst (not to mention patient) poisoning. Having said that many important intracellular processes are modulated by transition metals complexed in metalloproteins, with functions including storage and transport…

At the Scientific Update OPRD conference in Milan earlier this month, Xiaohu Deng from Kura Oncology discussed a pyrimidine-derived diazo intermediate that exists predominantly in the tautomeric ‘tetrazole’ form at equilibrium in solution.[1] The compound was shown as a putative retrosynthetic building block for synthesis of a J&J P2X7 antagonist (Figure 1).[2] I’d not come…

Antibacterial chemotherapy before the turn of the nineteenth century really was a brutal business. A fine line between killing bacteria or the host organism- the human population. Mercury and bismuth based ointments and elixirs were available from apothecaries and administered by quack doctors as remedies, most notably for syphilis- a sexually transmitted bacterial infection caused…

                    The naturally occurring cinchona alkaloids, and Quinine in particular, have been of interest to synthetic chemistry practitioners for many years, due ostensibly to its antimalarial activity, particularly against resistant strains of the disease. The original synthesis, by Woodward and Doering in 1944 was heralded as…

         2-Aminopyrides are useful synthetic intermediates and pharmacophores in a number of drugs.[1] The Chichibabin reaction, developed in the 1900’s gives a direct method for the amination of pyridine and pyridine derivatives (azines and azoles) using sodium or potassium amides. Intramolecular amination reactions are also known. The reaction can be run either…