p-Bromoacetophenone → HCID 24987026, compound

Temperature

0 °C

To a stirred solution of 1-methyl-2-cyanopyrrole (1.6 g, 15 mmol) and triisopropyl borate (7.0 mL, 30 mmol) in tetrahydrofuran (THF—45 mL) at 0° C. was added lithium diisopropylamide (LDA—2.0 M in heptane/THF/ethylbenzene, 13.3 mL, 26.6 mmol) in a dropwise fashion over 45 minutes. The resulting solution was stirred at 0° C. for 1 hour. To the solution was added 1-(4-bromophenyl)-ethanone (1.0 g, 5 mmol) dissolved in glyme (45 mL), sodium carbonate (1.59 g, 15 mmol) dissolved in water (9 mL), and tetrakis(triphenylphosphine)palladium (0) (0.28 g, 0.25 mmol). The resulting solution was heated to reflux for 1.5 hours. The solution was cooled to room temperature and partitioned between a saturated aqueous ammonium chloride solution (50 mL) and ethyl acetate (80 mL). The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a silica gel column (20% ethyl acetate in hexane) and triturated with ether to give 5-(4-acetylphenyl)-1-methyl-1H-pyrrole-2-carbonitrile as a yellow solid (0.62 g, 55%). MS (ES) m/z 225.1; HRMS: calcd for C14H12N2O+H+, 225.1022; found (ESI, [M+H]+), 225.1039.

1. temperatureThe resulting solution was heated
2. temperatureto reflux for 1.5 hours
3. temperatureThe solution was cooled to room temperature
4. custompartitioned between a saturated aqueous ammonium chloride solution (50 mL) and ethyl acetate (80 mL)
5. customThe organic layer was separated
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified on a silica gel column (20% ethyl acetate in hexane)
10. customtriturated with ether

ORD record

ord-b63703f113884eeeaaa47e6d16d9273f

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07319152B2