Ethyl Acetate → 1-(3-Bromo-5-(4-chlorophenyl)-4-methyl-1H-pyrrol-2-yl)propan-1-one

Temperature

-78 °C

A solution of N-bromosuccinimide (1.25 g, 7.06 mmol) in THF (20 ml) was added dropwise to a stirred solution of 1-(5-(4-chlorophenyl)-4-methyl-1H-pyrrol-2-yl)propan-1-one (compound 53a, 1.75 g, 7.06 mmol) in THF (40 ml) at about −78° C. The resulting reaction mixture was stirred at about −78° C. for 5 hr. The reaction mixture was then allowed to warm to 25° C. slowly during further 3 to 4 hr. The progress of the reaction was monitored by TLC. The solvent was evaporated from the reaction mixture under reduced pressure and to the residue so obtained was added ethyl acetate (200 ml). The mixture so obtained was washed with saturated sodium bicarbonate solution (1×50 ml) followed by washing with water (1×50 ml). The combined organic layer was then dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 10 ethyl acetate in hexanes to obtain the title compound (1.77 g, 77%)

1. customThe resulting reaction mixture
2. temperatureto warm to 25° C. slowly during further 3 to 4 hr
3. customThe solvent was evaporated from the reaction mixture under reduced pressure and to the residue
4. customso obtained
5. customThe mixture so obtained
6. washwas washed with saturated sodium bicarbonate solution (1×50 ml)
7. washby washing with water (1×50 ml)
8. dry with materialThe combined organic layer was then dried over anhydrous Na2SO4
9. customThe solvent was evaporated from the dried organic layer under reduced pressure
10. customto obtain a crude product, which
11. customwas then purified by flash column chromatography

ORD record

ord-ce7bc19bc8164405b1831b2e4a3d6ce9

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09072731B2