Boron trifluoride etherate → N-(4-{1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide

To a solution of 16 mg (0.04 mmol) of N-(4-{1-hydroxy-1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide (Example 7) in 1.5 mL CH2Cl2 at 0° C. were added 620 μL (3.88 mmol) of triethylsilane followed by 100 μL (0.79 mmol) of boron trifluoride diethyl etherate dropwise. The mixture was warmed to room temperature and stirred for 2.5 h. After this time, the reaction mixture was cooled to 0° C., quenched by the addition of a saturated aqueous solution of sodium bicarbonate, allowed to warm to room temperature, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 3:1) to give the title compound.

1. temperatureAfter this time, the reaction mixture was cooled to 0° C.
2. customquenched by the addition of a saturated aqueous solution of sodium bicarbonate
3. temperatureto warm to room temperature
4. extractionextracted with EtOAc
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 3:1)

ORD record

ord-bec3d449dbd64d999619eff62721c879

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473703B2