An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine

Abstract

An improved five-step synthesis of triethylene glycol-substituted 4-( N -methyl- N -Boc-amino)styrylpyridine ( 6 ) is described. Using cost-effective starting materials, the developed synthesis route was synthetic, efficient, and chromatographic purification-free. The key point of the work is the one-pot synthesis of tert -butyl methyl(4-vinylphenyl)carbamate through methylation and elimination in the NaH/THF system. The new synthesis route shows the potential to achieve scaled-up preparation of 6 in the future.

Mass Spectrometry Rearrangement Ions and Metabolic Pathway-Based Discovery of Indole Derivatives during the Aging Process in Citrus reticulata ‘Chachi’

“…N , N ′, O , O ′-Tetramethyl-leuko-indigo [ 60 , 61 ], N -methyl-3-hydroxyindole [ 62 ], N , N ′-demethylindigo, and N , N ′-demethylindirubin [ 63 , 64 ] were synthesized according to the reported schemes ( Scheme 1 ). The specific synthesis steps and the results of NMR and liquid chromatography–high-resolution tandem mass spectrometry (LC–HR–MS) are all described in the Supplementary Materials (Figure S1) .…”