反应详情

Imidazo[1,2-a]pyridine-3-carboxylic acid (62 mg, 0.38 mmol) was dissolved neat in thionyl chloride (112 mL, 1.5 mmol). The reaction mixture was stirred at ambient temperature for 1 hour before concentrating and drying under high vacuum for 16 hours. The resulting solid was dissolved in tetrahydrofuran (2 mL). 3-Methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (97 mg, 0.38 mmol) was added and the reaction was stirred at 70° C. in a sand bath for 6 hours. The mixture was concentrated and partitioned between ethyl acetate and saturated sodium bicarbonate. The ethyl acetate layer was washed with water and brine before drying over sodium sulfate and concentrating. Preparative Thin Layer Chromatography (Silica, 1 mm) of the crude material, eluting with 10% MeOH/DCM, gave N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (48 mg) in a band with Rf=0.6. MS m/z 397.3 (M+1, APCI+).

1. concentrationbefore concentrating
2. customdrying under high vacuum for 16 hours
3. dissolutionThe resulting solid was dissolved in tetrahydrofuran (2 mL)
4. stirringthe reaction was stirred at 70° C. in a sand bath for 6 hours
5. concentrationThe mixture was concentrated
6. custompartitioned between ethyl acetate and saturated sodium bicarbonate
7. washThe ethyl acetate layer was washed with water and brine
8. dry with materialbefore drying over sodium sulfate
9. concentrationconcentrating
10. washPreparative Thin Layer Chromatography (Silica, 1 mm) of the crude material, eluting with 10% MeOH/DCM