Water → 7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbaldehyde

Diisobutyl aluminum hydride (1.0M in toluene solution; 1.98 ml, 1.98 mmol) was added at −78° C. to a solution of 7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (300 mg, 099 mmol) prepared in Example 682 in anhydrous tetrahydrofuran (2 ml). The reaction mixture was stirred for 5 hours and then diluted with diethyl ether. Water (2 ml) and 15% sodium hydroxide solution (2 ml) were added to the reaction mixture, which was then stirred for 30 minutes. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 50.6 mg of the titled compound as a white solid. (Yield: 16%).

1. stirringwas then stirred for 30 minutes
2. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

ORD-Eintrag

ord-7dbb6da45a164d0aa59ed777b1cd8430

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08188114B2