ETHYL 3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE-5-CARBOXYLATE synthesis

4synthesis methods

Product Name:ETHYL 3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE-5-CARBOXYLATE
CAS Number:618070-51-2
Molecular formula:C14H16N2O3
Molecular Weight:260.29

229015-76-3 Synthesis

3-(4-METHOXYPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER

229015-76-3
26 suppliers
$45.00/50mg

74-88-4
350 suppliers
$15.00/10g

ETHYL 3-(4-METHOXYPHENYL)-1-METHYL-1H-PYRAZOLE-5-CARBOXYLATE

618070-51-2
21 suppliers
$75.00/250mg

Yield:618070-51-2 93%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20;

Steps:

4.1.9 Ethyl 3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carboxylate (7a)

To a solution of 1H-pyrazole 6a (455mg, 1.85mmol) and K₂CO₃ (384mg, 2.78mmol) in dry DMF (5mL) was added iodometane (0.17mL, 2.78mmol) at ambient temperature. The reaction mixture was stirred overnight at the same temperature and diluted with EtOAc. The organic phase was washed with water and brine, dried over MgSO₄, and concentrated in vacuo. Purification of the residue via flash column chromatography on silica gel (EtOAc/n-hexane=1:7) afforded 448mg (93%) of 1-methylpyrazole 7a as white solid with a melting point of 68-70°C: ¹H NMR (300MHz, CDCl₃) δ 7.67 (d, 2H, J=8.8Hz), 7.01 (s, 1H), 6.90 (d, 2H, J=8.8Hz), 4.35 (q, 2H, J=7.1Hz), 4.20 (s, 3H), 3.91 (s, 3H), 1.39 (t, 3H, J=7.1Hz); LRMS (FAB) m/z 261 (M+H⁺).

References:

Han, Young Taek;Kim, Kyeojin;Choi, Gyeong-In;An, Hongchan;Son, Dohyun;Kim, Hee;Ha, Hee-Jin;Son, Jun-Hyeng;Chung, Suk-Jae;Park, Hyun-Ju;Lee, Jeewoo;Suh, Young-Ger [European Journal of Medicinal Chemistry,2014,vol. 79,p. 128 - 142]