反应详情

温度

0 °C

This compound is prepared from compound 29, the product of Example 9, Step H. Tebbe reagent (μ-chloro-μ-methylene[bis(cyclopentadienyl)titanium]dimethyl-aluminum, 1 M solution in toluene, 0.12 mL, 0.12 mmol) was added to a solution of 7-(4-bromo-2-chloro-phenylamino)-8-chloro-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (29) (25 mg, 0.061 mmol) in THF (1 mL) cooled to 0° C. The reaction mixture was warmed to room temperature and stirred for 1.5 hours. HCl (10% aqueous solution, 1 mL) was added and the mixture stirred for 16 hours. The reaction was diluted with ethyl acetate, washed with saturated aqueous sodium carbonate, dried over MgSO4, and concentrated. The crude material was purified by flash column chromoatography (dichloromethane to 100:1 dichloromethane/methanol) to provide the desired product (6.8 mg, 28%). MS APCI (−) m/z 396, 398, 400 (M−, Cl, Br pattern) detected. 1H NMR (400 MHz, CDCl3) δ 9.05 (br s, 1H), 8.81 (s, 1H), 7.71 (s, 2H), 7.55 (d, 1H), 7.22 (dd, 1H), 6.55 (d, 1H), 2.67 (s, 3H).

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringthe mixture stirred for 16 hours
3. washwashed with saturated aqueous sodium carbonate
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customThe crude material was purified by flash column chromoatography (dichloromethane to 100:1 dichloromethane/methanol)