3,5-Dibromopyridine → 3-bromo-5-[(3R)-3-methoxypyrrolidin-1-yl]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dibromopyridine (0.644 g, 2.72 mmol), (R)-3-methoxypyrrolidine (0.25 g, 2.47 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.045 g, 0.05 mmol), sodium 2-methylpropan-2-olate (0.356 g, 3.71 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.077 g, 0.12 mmol) in degassed toluene (7.5 ml) was sealed into a microwave tube and stirred for 16 hours at 90 °C. The reaction was completed. After cooling, an aqueous solution of Na2CO3 was added. Extraction with DCM (twice). The organic layers were dried over MgSO4 and evaporated _in vacuo_ to give the crude product as an orange oil. PBO-04062-54-01 It was purified by chromatography (Merck cartridge SVF D26 - SI60 15-40 µm - 30 g) on silica gel eluting with EtOAc 0 to 25% in petroleum ether. Pure collected fractions were evaporated to afford (R)-3-bromo-5-(3-methoxypyrrolidin-1-yl)pyridine (0.325 g, 51.1 %) as a yellow oil. PBO-04062-54-02

Provenance & Evidence