Potassium Carbonate → tert-butyl 2-(4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate

Participants

Reaction Conditions

Reaction Steps

4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenol (3.02 g, 15.96 mmol), tert-butyl 2-bromoethylcarbamate (7.153 g, 2.0 eq) and potassium carbonate (4.412 g, 2.0 eq) were dissolved in 100 mL acetone and refluxed at 60° C. for 24 h. After reaction, the potassium carbonate was filtered and acetone was evaporated. The residue was dissolved in 100 mL DCM and extracted with 3×100 mL 1N NaOH. Purified by column chromatography (50-100% ethyl acetate in hexane) to afford the title compound as a yellow oil in 29.10% yield. LCMS m/z (%)=333 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ ppm 1.43 (s, 9H), 3.33 (q, J=5.05 Hz, 2H), 3.75 (s, 3H), 3.91 (t, J=5.05 Hz, 2H), 4.45-4.51 (m, 1H), 6.23 (d, J=2.02 Hz, 1H), 6.62 (d, J=3.03 Hz, 1H), 6.73 (dd, J=8.59, 3.03 Hz, 1H), 6.85 (d, 1H), 7.52 (d, J=2.02 Hz, 1H).

Provenance & Evidence