反应详情

温度

-20 °C

5-Fluoro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (146, 0.33 g, 0.79 mmol) and 1.5 mL of tetrahydrofuran were combined in a round bottom flask and cooled to −20° C. Isopropylmagnesium chloride (400 μL, 2.0 M in tetrahydrofuran, 0.8 mmol) was added dropwise and the reaction stirred and brought to −5° C. The reaction was cooled to −20° C. and 5-(3-chloro-benzylamino)-2-methyl-2H-pyrazole-3-carbaldehyde (145, 0.090 g, 0.36 mmol) in tetrahydrofuran was added and the reaction stirred and brought to 0° C. The reaction was concentrated under vacuum, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, then brine. The organic layer was separated and dried over sodium sulfate, filtered and the filtrate purified by silica gel flash column chromatography eluting with a gradient of 5-80% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=542.7, 543.95.

1. custombrought to −5° C
2. temperatureThe reaction was cooled to −20° C.
3. stirringthe reaction stirred
4. custombrought to 0° C
5. concentrationThe reaction was concentrated under vacuum
6. additiondiluted with ethyl acetate
7. washwashed with saturated aqueous sodium bicarbonate
8. customThe organic layer was separated
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customthe filtrate purified by silica gel flash column chromatography
12. washeluting with a gradient of 5-80% ethyl acetate in hexane
13. concentrationconcentrated under vacuum