Brc1cncc(Br)c1.CO[C@@H]1CCNC1>CC(C)(C)[O-].Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CO[C@@H]1CCN(c2cncc(Br)c2)C1
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
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