反应详情

温度

-20 °C

3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (68, 582.0 mg, 1.45 mmol, prepared as described in Example 22) was dissolved in tetrahydrofuran (10.0 mL) at −20° C. under an atmosphere of nitrogen. Isopropylmagnesium chloride in tetrahydrofuran (2.0 M, 0.79 mL) was added to the reaction. The reaction was stirred for 1 hour, during which the temperature rose to 0° C. The reaction was cooled to −20° C. and 2-chloro-4-(4-chloro-2-fluoro-benzyloxy)-5-methoxy-benzaldehyde (140, 200 mg, 0.61 mmol) in tetrahydrofuran (7.0 mL) was added. The reaction was stirred for 1.5 hours during which time the temperature rose to 0° C. The reaction was quenched with methanol and adsorbed onto silica, then purified by silica gel chromatography, eluting with 0-20% ethyl acetate:hexanes, to provide the desired compound (141, 318 mg, 87%). MS (ESI): [M+H+]+=603.3, 605.3.

1. customrose to 0° C
2. stirringThe reaction was stirred for 1.5 hours during which time the temperature
3. customrose to 0° C
4. customThe reaction was quenched with methanol
5. custompurified by silica gel chromatography
6. washeluting with 0-20% ethyl acetate