Data from: A 2nd-generation scalable synthesis of the HIV-1 entry inhibitor CJF-III-288 enabled by photoredox catalysis

Herein is reported the development and optimization of a 2nd-Generation
process synthesis for the human immunodeficiency virus-1 entry inhibitor
CJF-III-288 bis-trifluoroacetate salt 1. The key transformations of the
synthesis include a decatungstate-catalyzed diastereoselective Giese
addition to set the stereogenecity of the indoline core and install the
guanidine motif, followed by a high-yielding photoredox-nickel
dual-catalyzed Csp3–Csp2 cross coupling to append the methyl-amino methyl
aryl side chain. The route eliminates the use of noble metals, decreases
the step count nearly by half, reduces the number of flash column
purifications, and increases the overall yield of 1 tenfold. The route has
yielded 5.7 grams of 1 for use in in vivo studies.