S2 [(2-amino-4,5-dimethylthiophen-3-yl)(4-chloropheyl)methanone)] is an organic precursor to the (+)-enantiomer of JQ1, a break-through molecule in cancer research.  The purpose of this research was to synthesize enough of the S2 intermediate to continue the synthetic pathway of (+)-JQ1. The synthesis of S2 is similar to the Gewald reaction, where 2-butanone reacts with 4-chlorobenzoylacetonitrile (a-cyanoester) in the presence of elemental sulfur and morpholine (base) to yield the poly-substituted thiophene product. The resulting product was monitored by thin-layer chromatography and purified using recrystallization from ethanol/water and column chromatography. The product was characterized by proton NMR.

Synthesis of (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (S2) and ongoing synthesis of selective bromodomain inhibitor (+)-JQ1

245th National Meeting (2013)

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