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 (0.63g; 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-88837411efc847288ecca5b77efdb78a

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889706B2