Hexane → HCID 68048470, compound

A solution of nBuLi in hexane (2.5 M, 70 mL, 0.176 mol) was added to a solution of 5-bromo-2-isobutoxy-pyridine (Preparation 8, 27 g, 0.117 mol) in THF (300 mL) under a nitrogen atmosphere at −78° C. After stirring for 1 hour, trimethyl borate (18.3 g, 0.176 mol) was added. The mixture was stirred at 0° C. for 1 hour then diluted with 3N NaOH (15 mL) and hydrogen peroxide (30%, 175 mL). The resulting mixture was stirred at room temperature for 1 hour and extracted with EtOAc (3×500 mL). The combined organics were washed with saturated aqueous sodium sufite (3×500 mL), brine (300 mL) then dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield the crude product that was purified by silica gel chromatography (petroleum ether/EtOAc 100:1 to 10:1) to give the title compound as an off-white solid (6.0 g).

1. stirringThe mixture was stirred at 0° C. for 1 hour
2. stirringThe resulting mixture was stirred at room temperature for 1 hour
3. extractionextracted with EtOAc (3×500 mL)
4. washThe combined organics were washed with saturated aqueous sodium sufite (3×500 mL), brine (300 mL)
5. dry with materialthen dried over sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. customto yield the crude product that
9. customwas purified by silica gel chromatography (petroleum ether/EtOAc 100:1 to 10:1)

ORD record

ord-8ab39c76fc224dafb2ce538fea94828e

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772343B2