Potassium Carbonate → 6-chloro-5-[2-(dimethylamino)pyrimidin-5-yl]-1H-indole-3-carbaldehyde

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (150 mg, 0.57 mmol) in anhydrous 1,4-dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (145 mg, 1.13 mmol). The reaction mixture was stirred at room temperature for 20 minutes to give a thick solution. The reaction mixture was then treated with 2N aqueous potassium carbonate (393 mg, 2.85 mmol), 5-bromo-N,N-dimethylpyrimidin-2-amine (115 mg, 0.57 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg, 0.068 mmol) and degassed with nitrogen for 2 minutes. The reaction mixture was heated to 90° C. for 30 minutes. After cooling to room temperature, the solvents were removed in vacuo and the residue was purified by column chromatography on silica gel (EtOAc/petroleum ether=1:5 to 1:1) to afford 6-chloro-5-[2-(dimethylamino)pyrimidin-5-yl]-1H-indole-3-carbaldehyde (100 mg, 58.3% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.25 (s, 1H), 9.92 (s, 1H), 8.40 (s, 2H), 8.36 (s, 1H), 8.01 (s, 1H), 7.69 (s, 1H), 3.15 (s, 6H).

1. customto give a thick solution
2. customdegassed with nitrogen for 2 minutes
3. temperatureThe reaction mixture was heated to 90° C. for 30 minutes
4. temperatureAfter cooling to room temperature
5. customthe solvents were removed in vacuo
6. customthe residue was purified by column chromatography on silica gel (EtOAc/petroleum ether=1:5 to 1:1)

ORD-Eintrag

ord-c121c62d56234088a67df93722dbdd3e

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889730B2