Potassium Carbonate → 5-Amino-3-tert-butyl-pyrazol-1-yl-phenol

A mixture of 5-tert-butyl-2H-pyrazol-3-ylamine (1 g, 7.18 mmol), 3-iodophenol (1.74 g, 7.90 mmol), copper (I) iodide (68 mg, 0.36 mmol), (1S,2S)—N,N′-dimethyl cyclohexane-1,2-diamine (204 mg, 1.44 mmol) and potassium carbonate (2.08 g, 15.09 mmol) in toluene (8 mL) was de-gassed and flushed with argon (3×). The reaction mixture was then treated with microwave irradiation, at 150° C. for 1 h. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL). The aqueous layer was extracted with a further 20 mL EtOAc and the combined organic layers were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue obtained was purified by FCC, using 0-100% EtOAc in cyclohexane to afford the title compound as a brown gum (1.42 g, 86%). LCMS (Method 3): Rt 2.21 min, m/z 232 [MH+].

1. customwas de-gassed
2. customflushed with argon (3×)
3. additionThe reaction mixture was then treated with microwave irradiation, at 150° C. for 1 h
4. additionThe mixture was diluted with EtOAc (20 mL)
5. washwashed with water (20 mL)
6. extractionThe aqueous layer was extracted with a further 20 mL EtOAc
7. washthe combined organic layers were washed with brine (20 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue obtained
12. customwas purified by FCC

ORD-Eintrag

ord-66a4404cfae64083891ae5b56d142958

Quelldatensatz

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09139584B2