反应详情

温度

-20 °C

In a round bottom flask, 5-chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (4, 1.7 g, 3.9 mmol) was combined with 1.3 mL of tetrahydrofuran and cooled to −20° C. Isopropylmagnesium chloride (2.0 mL, 2 M in tetrahydrofuran, 4.0 mmol) was added dropwise and the reaction stirred at −5° C. The reaction was cooled to −20° C. and 5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazole-3-carbaldehyde (113, 0.622 g, 1.83 mmol) in 2 mL of tetrahydrofuran was added and the reaction stirred at 0° C. The reaction was concentrated under vacuum, diluted with ethyl acetate and washed with sodium bicarbonate and brine. The organic layer was dried with sodium sulfate and purified by silica gel column chromatography, eluting with 5-80% ethyl acetate in hexanes. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=648.38 and 649.74.

1. temperatureThe reaction was cooled to −20° C.
2. stirringthe reaction stirred at 0° C
3. concentrationThe reaction was concentrated under vacuum
4. additiondiluted with ethyl acetate
5. washwashed with sodium bicarbonate and brine
6. dry with materialThe organic layer was dried with sodium sulfate
7. custompurified by silica gel column chromatography
8. washeluting with 5-80% ethyl acetate in hexanes
9. concentrationconcentrated under vacuum