Sodium hydride → 2-(1-[(benzyloxy)methyl]-5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-5-bromopyridine

Temperature

0 °C

To a solution of 5-bromo-2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine (3.00 g) in N,N-dimethylformamide (25 mL) was added sodium hydride (60%, oil, 279 mg) under ice-cooling, and the mixture was stirred at 0° C. for 10 min. To the reaction solution was added [(chloromethoxy)methyl]benzene (0.970 mL), and the mixture was stirred at 0° C. for 3 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50, volume ratio) to give the title compound (2.91 g, yield 79%) as a colorless amorphous solid.

1. temperaturecooling
2. stirringthe mixture was stirred at 0° C. for 3 hr
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed successively with water and saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50, volume ratio)

ORD record

ord-e2dc8e2f2e404cd89ee94252aa15663e

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318746B2