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With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 120℃; for 48h;
To a solution of Part A Compound (469 mg, 2.15 mmol) in DMF (4 mL) was added 1-fluoro-4-(methylsulfonyl)benzene (562 mg, 3.23 mmol) at RT, followed by K2CO3 (891 mg, 6.45 mmol). The mixture was heated at 120° C. for 48 h, then was cooled to RT. The mixture was diluted with EtOAc (50 mL), washed with H2O (20 mL) and brine (2.x.10 mL), dried (MgSO4) and concentrated in vacuo. The residual red oil was chromatographed (SiO2; 40 g; continuous gradient from 100percent hex to 2:3 hex:EtOAc over 40 min, then held at 2:3 hex:EtOAc for 10 min) to give Part B Compound (474 mg, 59percent yield) as a beige solid. LCMS Method A (ESI, positive ion spectrum): (M+H)/z=374, tR=3.23 min.
INTERMEDIATE 6 3-Iodo-l-(4-(methylsulfonyl)phenyl)-lH-pyrazole To a solution of <strong>[4522-35-4]3-iodopyrazole</strong> (0.7 g, 3.61 mmol) in DMSO (18.0 mL) was added sodium hydride (60% disp. in oil, 0.173 g, 4.33 mmol) and the resulting mixture was stirred for 0.5 h before adding 4-methylsulfoylfluorobenzene (0.629 g, 3.61 mmol). The reaction mixture was stirred at 90 C for 3 h. The reaction was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flas chromatography (ISCO, 40 g, 0-60 % EtOAc in hexanes) to afford 3-iodo-l-(4-(methylsulfonyl)phenyl)-lH-pyrazole, as a white solid. LCMS calc. = 348.94; found = 348.92 (M+H)+. 1H NMR (500 MHz, CDC13): delta 8.03 (dd, J= 8.7, 1.7 Hz, 2 H); 7.89 (dd, J= 8.7, 1.7 Hz, 2 H); 7.84 (d, J= 2.6 Hz, 1 H); 6.69 (d, J= 2.6 Hz, 1 H); 3.09 (s, 3 H).
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