Potassium Carbonate → 2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]acetamide

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 1,4-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 mmol), 2-(4-bromophenoxy)acetamide (240 mg, 1.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg). The sealed vial 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 layers were dried and concentrated in vacuo to give 2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]acetamide (250 mg, 55% yield) as a yellow solid.

1. customwas sealed in a reaction vessel
2. customto give a white slurry
3. customThe sealed vial 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 layers were dried
8. concentrationconcentrated in vacuo

ORD-Eintrag

ord-554af53e4f9949389bb5a098541b43aa

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889730B2