Acetic Acid → ethyl 5-methoxy-1-(5-((3-methoxypropyl)carbamoyl)pyridin-2-yl)-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Combined ethyl 5-hydroxy-1-(5-((3-methoxypropyl)carbamoyl)pyridin-2-yl)-1H-pyrazole-4-carboxylate (2.2 g, 6.32 mmol), MeOH (5 mL), and DCM (50 mL) and added 2.0 M TMS-diazomethane in hexanes (4.42 mL, 8.84 mmol) (over about 10 minutes) and stirred at 20° C. for 20 min. The reaction was then quenched with acetic acid (0.145 mL, 2.53 mmol) and concentrated in vacuo to give a residue which was purified on an 80 g silica gel column eluted with 10 to 100% EtOAc in hexanes to give the title compound (2.0 g, 87% yield) as a white solid. MS m/z 363 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (t, J=7.1 Hz, 3H) 1.78 (quin, J=6.6 Hz, 2 H) 3.25 (s, 3 H) 3.30-3.37 (m, 2 H) 3.39 (t, J=6.3 Hz, 2 H) 4.14 (s, 3 H) 4.27 (q, J=7.1 Hz, 2 H) 7.79 (dd, J=8.5, 0.6 Hz, 1 H) 8.03 (s, 1 H) 8.39 (dd, J=8.5, 2.4 Hz, 1 H) 8.76 (t, J=5.6 Hz, 1 H) 8.98 (dd, J=2.4, 0.6 Hz, 1 H).

Provenance & Evidence