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6-bromo-1-(6-chloro-2-methoxypyrimidin-4-yl)-5-methyl-1H-indazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
57.3%
With caesium carbonate; In N,N-dimethyl-formamide; at 120.0℃; for 1.5h;Microwave irradiation;
6-Bromo-5-methyl-1 H-indazoie (50 mg, 0.237 mmol) and 4,6-dichloro-2-methoxypyrimidmne (127 mg, 0.711 mmol) was dissolved in DMF (3 mL), Cs2CO3 (154 mg, 0.474 mmol) was added and the mixture was stirrd at 120 °C for 1.5 h under microwave irradiation. Water (20 mL) and EtOAc (50 mL) were added to the reaction mixture. The layers were seperated and the aqueous layer was extracted by EtOAc (30 mL). The combined organic layers waswashed with saturated aqueous NaCI (50 mL x 2 times), dried over anhydrous Na2SO4 and then concentrated under the reduced pressure. The residue was purified by normal phase chromatography (ISCO, 24g column, PE: EtOAc= 100:0 --> 80:20) to afford 6-bromo-1-(6- chloro-2-methoxypyrimidin-4-yI)-5-methyl-1 H-indazole (48 mg, 0.136 mmol, 57.3 percent yield) as a white solid.LCMS: (mobile phase: 5-95percent acetonitrile), Rt = 4.47 mm in 5 mm; MS Calcd: 352; MSFound: 353 [M+1].1H NMR (DMSO-d6): 8.92 (s, 1H), 8.59 (s, 1H), 7.93 (s, IH), 7.60 (s, 1H), 4.08 (s, 3H)(Note:a CH3 peak is masked by the solvent DMSO)