2-Chloropyridine → HCID 67258949, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-{[(3R,4R)-3-(3-ethoxy-4-methoxyphenyl)tetrahydro-2H-thiopyran-4-yl]carbamoyl}benzoate (2.58 g; compound C11) and 2-chloropyridin (0.68 ml) in toluene (60 ml) is slowly added a solution of POCl3 (1.65 ml) in toluene (6 ml). The reaction mixture is stirred for 12 h at 100° C. The reaction mixture is allowed to come to RT and then quenched by slow addition of water (15 ml). Additional water (30 ml) is added and the pH is adjusted to about 9 by addition of 5 M aqueous solution of sodium hydroxide. The organic phase is separated and the aqueous phase is extracted with toluene (30 ml). The combined organic phases are dried over sodium sulfate and the solvent is removed in vacuo. The resulting residue is purified flash column chromatography [silica gel, eluation gradient: cyclohexane/EtOAc, 3/1 to 1/1 (v/v)] to yield the title compound as a solid.

Provenance & Evidence