Acetic Acid → HCID 58095178, compound

Temperature

40 °C

To a solution of 4-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl]-2-methylpyridine (115 mg, 0.26 mmol) in DCM (10.0 mL) was added phenylsilane (0.16 mL, 1.28 mmol), acetic acid (0.66 mL, 11.5 mmol), and tetrakis(triphenylphosphine)palladium (14.8 mg, 0.01 mmol) at room temperature then the mixture was stirred for 2 h at 40° C. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residual acetic acid was quenched by addition of saturated NaHCO3 (50 mL). The mixture was extracted with DCM (3×70 mL), and the combined DCM layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, elution with 3-5% MeOH in DCM) to give crude product which was further purified by column chromatography (SiO2, elution with 100% EtOAc) to provide 51 mg of product (49% yield). LC/MS (FA) ES+ 388. 1H NMR (400 MHz, d6 DMSO) δ: 11.7 (br s, 1H), 8.46 (d, J=5.3 Hz, 1H), 7.76 (s, 1H), 7.72 (d, J=2.1 Hz, 1H), 7.57 (br s, 1H), 7.46-7.50 (m, 2H), 7.41 (d, J=8.3 Hz, 1H), 7.10 (br s, 1H), 6.95 (br s, 1H), 2.49 (s, 3H).

1. temperatureAfter cooling to room temperature
2. customthe solvent was evaporated under reduced pressure
3. customthe residual acetic acid was quenched by addition of saturated NaHCO3 (50 mL)
4. extractionThe mixture was extracted with DCM (3×70 mL)
5. dry with materialthe combined DCM layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography (SiO2, elution with 3-5% MeOH in DCM)
9. customto give crude product which
10. customwas further purified by column chromatography (SiO2, elution with 100% EtOAc)

ORD record

ord-4645bf9d462d46f3b161d84fd506ced5

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139589B2