Potassium Carbonate → 2-phenyl-2-[4-(1H-pyrazol-4-yl)phenyl]ethanamine

Temperatur

135 °C

To a suspension of 2-(4-chlorophenyl)-2-phenylethylamine hydrochloride (134 mg, 0.5 mmol, 1.0 equiv.) (Array PPA-Q02-1) in toluene (0.8 ml) was added bis(tri-t-butylphosphine)palladium (0) (3 mg, 1 mol %) (Strem) and the mixture was purged with nitrogen. A suspension of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (107 mg, 0.55 mmol, 11 equiv.) (Aldrich 52,505-7) in ethanol (0.8 ml) was added followed by potassium carbonate (415 mg, 3.0 mmol, 6 equiv.) in water (2.5 ml). The mixture was purged with nitrogen and sealed. The reaction mixture was heated in a CEM Explorer™ microwave to 135° C. for 15 minutes using 50 watts power. The solvents were removed and the residue was partitioned between ethyl acetate and 2N NaOH. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography (SiO2), eluting with a mixture of dichloromethane (90 ml):methanol (18 ml):acetic acid (3 ml):H2O (2 ml) to afford the title compound 14 mg (9%); LCMS (PS-A) Rt 1.79 min; m/z [M+H]+ 264.

1. customthe mixture was purged with nitrogen
2. additionwas added
3. customThe mixture was purged with nitrogen
4. customsealed
5. customThe solvents were removed
6. customthe residue was partitioned between ethyl acetate and 2N NaOH
7. extractionThe aqueous layer was extracted with ethyl acetate
8. washthe combined organic layers were washed with brine
9. dry with materialdried (MgSO4)
10. concentrationconcentrated under reduced pressure
11. customThe crude reaction mixture
12. customwas purified by column chromatography (SiO2)
13. washeluting with a mixture of dichloromethane (90 ml)

ORD-Eintrag

ord-6fa1fd2224354fa99eea5f628ca172ae

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09283226B2