The development work toward the robust and efficient manufacturing process to vismodegib, the active pharmaceutical ingredient (API) in Erivedge, is described. The optimization of the four-stage manufacturing process was designed to produce the API with the required critical quality attributes: (1) the selective catalytic hydrogenation reduction of the nitro compound 3 to the corresponding aniline 4 while minimizing the formation of potential genotoxic (mutagenic) impurities; (2) the control of the polymorphic phase and multipoint specification for particle size distribution.

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Several new 4.7-donor substituted 1.10-phenanthrolines were synthesized and the corre­sponding tris(1,10-phenanthroline)iron(II) complexes were studied by cyclic voltammetry. All iron(II) complexes showed fully reversible waves at scan rates between 50 and 500 mV/s. For some redox systems the kinetics in their reaction with chlorine was studied. Complexes 7k and 71 significantly extent the potential range of tris(1,10-phenanthroline)iron(II) complexes.

The α-Umpolung of ketones and aldehydes via their silyl enol ether cation radicals has been developed and tested for the use of different nucleophiles.

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