تفاعل #8179

معادلة التفاعل

methyl 5-(4-methylthiophenyl)-1-(2-pyridyl)pyrazole-3-carboxylate

dibromomethane

methyllithium

→

title compound

المردود 69.0%

2-Bromo-1-(5-(4-methylthiophenyl)-1-(2-pyridyl)pyrazol-3-yl)ethan-1-one

المردود 69.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solution was quenched with aqueous sodium bicarbonate
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   تجفيفThe combined organic extracts were dried over sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated

الإجراء التجريبي

To a stirred solution of methyl 5-(4-methylthiophenyl)-1-(2-pyridyl)pyrazole-3-carboxylate (prepared as described in Penning, T. D. et al. J. Med. Chem. 1997, 40, 1347–1365.; 0.39 g, 1.2 mmol) and dibromomethane (0.17 mL, 2.4 mmol) in THF (10 mL) at −78° C. under nitrogen atmosphere was added methyllithium (1.6 M in ether, 1.4 mL, 2.2 mmol). After being stirred at the same temperature for 90 minutes, the solution was quenched with aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Chromatography of the residue on silica gel (2:1 EtOAc:hexane) gave the title compound (0.32 g, 69% yield) as a white foam. 1H NMR (300 MHz, CDCl3) δ 8.42–8.40 (m, 1H), 7.83 (m, 1H), 7.55–7.51 (m, 1H), 7.17–7.09 (m, 4H), 7.02 (s, 1H), 4.70 (s, 2H), 2.46 (s, 3H); LRMS (API-TIS) m/z 388 and 390 (MH+).

المصدر