Potassium Carbonate → 6-chloro-5-[4-(1-methylpyrrolidin-3-yl)phenyl]-1H-indole-3-carbaldehyde

To 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (118 mg, 0.446 mmol) in anhydrous 1,4-dioxane (3.7 mL) and anhydrous DMF (0.74 mL) was added N,N-dimethylformiminium chloride (114 mg, 0.892 mmol). The reaction mixture was stirred for 10 min at room temperature, yielding a thick suspension. The reaction mixture was treated with 2N aqueous potassium carbonate (1.1 mL, 2.2 mmol), 3-(4-bromophenyl)-1-methylpyrrolidine (120 mg, 0.446 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (26 mg, 0.036 mmol). The resulting mixture was heated at 90° C. for 30 min. The reaction mixture was cooled and partitioned between water and EtOAc. The aqueous phase was extracted twice with EtOAc, and the combined organic phases were dried over sodium sulfate and concentrated in vacuo to give 6-chloro-5-[4-(1-methylpyrrolidin-3-yl)phenyl]-1H-indole-3-carbaldehyde (0.23 g, 16% yield) which was used directly in the next step. MS (ES+) 339.0 (M+H)+.

1. customyielding a thick suspension
2. temperatureThe resulting mixture was heated at 90° C. for 30 min
3. temperatureThe reaction mixture was cooled
4. custompartitioned between water and EtOAc
5. extractionThe aqueous phase was extracted twice with EtOAc
6. dry with materialthe combined organic phases were dried over sodium sulfate
7. concentrationconcentrated in vacuo

ORD-Eintrag

ord-0d660c52160d407ab2ca323f19e861c1

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889730B2