Ethanol → 6-Chloro-1H-indole-3-carboxaldehyde

Temperatur

110 °C

To a solution of 1-{3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenoxy]azetidin-1-yl}ethanone (130 mg, 0.43 mmol) in toluene (5 mL) was added 5-bromo-6-chloro-1H-indole-3-carbaldehyde (134 mg, 0.52 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (32 mg, 0.045 mmol), and 2M aqueous potassium carbonate (0.86 mL, 1.72 mmol) and ethanol (1.7 mL). The mixture was degassed with nitrogen for 3 min and heated to 110° C. by microwave irradiation for 1 h. The mixture was concentrated in vacuo to give a residue, which was dissolved with ethyl acetate (50 mL) and washed with brine (2×15 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a brown residue, which was purified by flash chromatography (petroleum ether/ethyl acetate=20:1 to 4:1) to give [(1-acetylazetidin-3-yl)oxy]phenyl}-6-chloro-1H-indole-3-carbaldehyde (70 mg, 44%) as a yellow solid.

1. customThe mixture was degassed with nitrogen for 3 min
2. concentrationThe mixture was concentrated in vacuo
3. customto give a residue, which
4. washwashed with brine (2×15 mL)
5. dry with materialThe organic layer was dried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customto give a brown residue, which
8. customwas purified by flash chromatography (petroleum ether/ethyl acetate=20:1 to 4:1)

ORD-Eintrag

ord-7aab25856abc4aeb8403ebd6eb1c7067

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889730B2