N-bromobutanimide → HCID 121282944, compound

Temperature

-78 °C

To a stirred solution of 1-(5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrol-2-yl)-2-cyclopropylethanone (Step 1)(0.30 g, 1.04 mmol) in THF (10 ml) at −78° C. was added a solution of N-bromosuccinimide (0.18 g, 1.04 mmol) in THF (10.0 ml) in a drop wise manner. The resulting mixture was stirred at −78° C. for 10 min. The progress of the reaction was monitored by TLC. The reaction mixture was quenched by the addition of a saturated sodium bicarbonate solution (5 ml). The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (30 ml). The organic layer was washed with a saturated sodium bicarbonate solution (1×10 ml) followed by water (1×10 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain a crude product which was purified by column chromatography using 10% ethyl acetate in hexanes to obtain the title compound 4(0.34 g, 89.0%). MS: m/z 367 (M+1).

1. customThe reaction mixture was quenched by the addition of a saturated sodium bicarbonate solution (5 ml)
2. customThe solvent was evaporated under reduced pressure
3. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
4. washThe organic layer was washed with a saturated sodium bicarbonate solution (1×10 ml)
5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
6. customThe solvent was evaporated under reduced pressure
7. customto obtain a crude product which
8. customwas purified by column chromatography

ORD record

ord-35666bf7e8b5442f8dc7ea44a736ed3b

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447037B2