1H-Pyrazole-4-carboxylic acid, 1-(4-fluorophenyl)-3-(4-methylphenyl)- synthesis
- Product Name:1H-Pyrazole-4-carboxylic acid, 1-(4-fluorophenyl)-3-(4-methylphenyl)-
- CAS Number:956779-12-7
- Molecular formula:C17H13FN2O2
- Molecular Weight:296.3
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Yield:956779-12-7 72%
Reaction Conditions:
with Jones reagent in acetone at 20;Inert atmosphere;
Steps:
11
To a solution of 2a (0.21 g, 0.75 mmol) dissolved in 16 mL of acetone, 5 mL of Jones' reagent was added.
The reaction mixture was stirred at room temperature and monitored by TLC.
The reaction mixture was poured into water and extracted with EtOAc.
The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated in vacuo to afford 0.16 g (72%) of the title acid: mp 202.0 °C. 1H NMR (CDCl3) δ 8.51 (s, 1H), 7.75 (m, 3H), 7.32 (d, 2H), 7.18 (t, 4H), 2.41 (s, 3H).
13C NMR (CDCl3) δ 170.7, 164.5, 155.9, 140.6, 135.1, 132.6, 130.9, 130.6, 130.2, 130.1, 122.8, 118.2, 22.7. Anal. Calcd for C17H13FN2O2: C, 68.91; H, 4.41; N, 9.45. Found: C, 68.13; H, 4.43; N, 8.94.
References:
Yu, Donna D.;Lin, Wenwei;Forman, Barry M.;Chen, Taosheng [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 11,p. 2919 - 2938]
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