2-Bromopyridine → HCID 70032920, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.68 g (1 mmol) (2S,4R)-5-Bromo-2-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine, 0.28 g (1.1 mmol) bis(pinacolato)diboron, 0.29 g (3 mmol, dried 2 h at 100° C., 0.1 Torr) potassium acetate and 0.024 g (0.03 mmol) PdCl2(dppf) in 12 ml DMF were stirred for 4.5 h at 80° C. The reaction was cooled, treated with 0.195 ml (2 mmol) 2-bromopyridine, 0.024 g (0.03 mmol) PdCl2(dppf) and 2.5 ml aqueous 2 M Na2CO3 solution and heated for 16 h at 80° C. The reaction evaporated (60° C./0.1 torr) and partitioned between water/Et2O (3×). The organic phases were washed with aqueous 10% NaCl and dried over Na2SO4. Purification by flash-chromatography on silica gel (toluene/EtOAc 97.5:2.5) gave 0.125 g (2S,4R)-5-Pyridin-2-yl-2-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine, MS: 675 (MH+). TFA/triisopropylsilane deprotection (see General method for S-deprotection, Method D) gave (3R,5S)-1-(5-Pyridin-2-yl-pyrimidin-2-yl)-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol; compound with trifluoro-acetic acid, MS: 433 (MH+).

Provenance & Evidence