反应详情

A mixture of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (260 mg, 1.00 mmol) and N,N-dimethylformiminium chloride (250 mg, 2.00 mmol) in dry dioxane (5 mL) and DMF (1 mL) was sealed in a reaction vessel and stirred at room temperature for 10 minutes to give a white slurry. To the slurry was added 2M aqueous potassium carbonate (2.5 mL, 5.0 mmol), [1-(4-bromophenyl)cyclobutyl]methanol (240 mg, 1.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg). The reaction mixture was degassed with nitrogen and heated to 90° C. for 30 minutes. The reaction was quenched with water (20 mL) and extracted with EtOAc (3×20 mL). The combined organic phases were dried and concentrated in vacuo to give 6-chloro-5-{4-[1-(hydroxymethyl)cyclobutyl]phenyl}-1H-indole-3-carbaldehyde (180 mg, 68% yield), which was used into next step without further purification.

1. customwas sealed in a reaction vessel
2. customto give a white slurry
3. customThe reaction mixture was degassed with nitrogen
4. temperatureheated to 90° C. for 30 minutes
5. customThe reaction was quenched with water (20 mL)
6. extractionextracted with EtOAc (3×20 mL)
7. customThe combined organic phases were dried
8. concentrationconcentrated in vacuo