反应详情

温度

0 °C

1-((6-Isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine (Preparation D; 0.673 g, 2.40 mmol) and ethyl 7-fluoroimidazo[1,2-a]pyridine-3-carboxylate (Step C, 0.500 g, 2.40 mmol) were dissolved in dry THF (24 mL) and chilled to 0° C. LiHMDS (5.28 mL, 5.28 mmol, 1M in THF) was added by syringe over a five-minute period. Once the addition was complete, the reaction mixture was removed from the cooling bath and allowed to warm to ambient temperature. The mixture was quenched with saturated ammonium chloride solution and extracted with EtOAc. The combined organic extracts were washed with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated. The crude material was purified by column chromatography (100% ethyl acetate) to afford 775 mg (73%) of 7-fluoro-N-(1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide.

1. additionOnce the addition
2. customthe reaction mixture was removed from the cooling bath
3. temperatureto warm to ambient temperature
4. customThe mixture was quenched with saturated ammonium chloride solution
5. extractionextracted with EtOAc
6. washThe combined organic extracts were washed with saturated sodium bicarbonate solution
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customThe crude material was purified by column chromatography (100% ethyl acetate)