2-((4-Chlorophenyl)Sulfonyl)Nicotinaldehyde(WXC03056) synthesis

Yield:1161864-76-1 61%

Reaction Conditions:

in dimethyl sulfoxide at 100; for 72 h;

Steps:

3 2-(4-Chlorobenzenesulfonyl)-pyridine-3-carboxaldehyde

2-(4-Chlorobenzenesulfonyl)-pyridine-3-carboxaldehyde 2-Chloro-3-pyridinecarboxaldehyde (5.0 g, 35.0 mmol) and 4-chlorobenzenesulfinic acid sodium salt (7.75 g, 38.8 mmol) were dissolved in DMSO (120 ml) and the mixture was heated at 100° C. for 72 h under nitrogen. Upon cooling to ambient the mixture was diluted with water (500 ml) and extracted with EtOAc (3*). The combined organics were washed with water, brine, dried (MgSO₄) and evaporated to dryness to afford 8.1 g of crude material. The crude compound was pre-absorbed onto silica and purified by dry pad suction column chromatography, eluding with heptane using an EtOAc gradient, to afford 4.62 g (61%) of the desired product as a white powdery solid (MP=100.5-101° C.; IR=1698 cm^-1; HPLC=8.00 min >99%). ¹H NMR (400 MHz; CDCl₃): 7.56 (1H, dd) 7.60 (1H, dd) 7.99 (1H, dd) 8.38 (1H, dd) 8.67 (1H, dd) 11.1 (1H, s). ¹³C NMR (100 MHz, CDCl₃): 127.3 (d) 129.6 (d) 130.8 (s) 131.1 (d) 136.5 (s) 138.0 (d) 141.4 (s) 152.5 (d) 159.5 (s) 188.4 (d).

References:

US2009/186923,2009,A1 Location in patent:Page/Page column 11