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

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (150 mg, 0.57 mmol) in dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (155 mg, 1.21 mmol). The reaction mixture was stirred at room temperature for 20 min. 2 N potassium carbonate (314 mg, 2.28 mmol), 3-(4-bromophenoxy)propanoic acid (139 mg, 0.57 mmol) and Pd(dppf)Cl2 (21 mg, 0.028 mmol) were then added. The reaction was degassed with N2 and heated to 90° C. for 30 min. The reaction was extracted with ethyl acetate (10 mL×2). The organic layers were washed with brine (10 mL), dried over sodium sulfate, and concentrated to give the title compound (170 mg, 87% yield) as a brown oil.

1. customThe reaction was degassed with N2
2. temperatureheated to 90° C. for 30 min
3. extractionThe reaction was extracted with ethyl acetate (10 mL×2)
4. washThe organic layers were washed with brine (10 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated

ORD-Eintrag

ord-8463d63c20914b44893ec01cffa9c0b9

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09394285B2