3-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine → HCID 59371575, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine (346 mg, 0.97 mmol) and 4-[2-(4-chlorobenzyloxy)ethyl]piperidine (270 mg, 1.06 mmol, 1.1 equiv.) in anhydrous toluene (6 mL) were added successively sodium tert-butoxide (139 mg, 1.45 mmol, 1.5 equiv.), tris(dibenzylideneacetone)dipalladium(0) (17.7 mg, 19 μmol, 0.02 equiv.), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 33.6 mg, 58 μmol, 0.06 equiv.). The mixture was degassed and purged with Ar (3 cycles), then warmed to 98-100° C. for 4 h. After cooling to room temperature, the mixture was diluted with EtOAc, and the solution was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by CC on SiO2 with CH2Cl2/EtOAc 4:1, then 1:1. After evaporation, 3-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]-5-[4-[2-(4-chlorobenzyloxy)ethyl]-1-piperidinyl]pyridine (437 mg, 85%) was obtained as a pale yellow oil.

Provenance & Evidence