Potassium Carbonate → (E)-ethyl 3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylate

Temperatur

80 °C

To a solution of compound 4.0 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.7 g, 5 mmol, 1 equiv.) in dioxane (20 mL) at room temperature was added triethyl phosphonoacetate (3 mL, 15 mmol, 3 equiv.) and K2CO3 (3.45 g, 25 mmol, 5 equiv.). The resulting mixture was heated overnight at 80° C. under argon. Upon cooling to room temperature, the mixture was diluted with EtOAc (50 mL) and washed with water (50 mL) and brine (50 mL). The organic phase was dried over Na2SO4, after removal of solvent under vacuum. The resulting residue was purified with flash chromatography (Hexanes: EtOAc=6:1) to afford the desired product 4.1 (E)-ethyl 3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylate (0.63 g; 50%). LC-MS: (M+H) 251.29

1. temperatureUpon cooling to room temperature
2. washwashed with water (50 mL) and brine (50 mL)
3. dry with materialThe organic phase was dried over Na2SO4
4. customafter removal of solvent under vacuum
5. customThe resulting residue was purified with flash chromatography (Hexanes: EtOAc=6:1)

ORD-Eintrag

ord-b4a449153b8245ecbafd72c5fa02982e

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08394818B2