Raltegravir (free base) Selective N- v’s O- alkylation of an amide can be challenging and somewhat unpredictable- the outcome being highly dependent on the structure of the substrate. A good example of this is the N-methylated pyrimidone intermediate (5) en route to Merck’s antiretroviral drug Raltegravir.1 Direct methylation of amide (4) (Figure 1) using MeI gives significant
Month: January 2019
Lithium (Li, Element 3) Lithium, first member of the group 1 alkali metals, was discovered in 1817 by Johan August Arfwedson. It’s been around since the dawn of (astronomical) time- both stable isotopes, Li6 and Li7, being among a small handful of elements created in the Big Bang.1Terrestrially its highly abundant in seawater (up to
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
