Potassium Phosphate, Tribasic → 1-(5-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-1H-indole-3-carboxylic acid ethyl ester

Temperature

110 °C

To a suspension of 3-bromo-5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridine (2.0 g, 5.5 mmol), 1H-Indole-3-carboxylic acid ethyl ester (1.3 g, 6.6 mmol), copper iodide (0.11 g, 0.55 mmol), K3PO4 (2.5 g, 11.6 mmol) in toluene (5 mL) was added (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.16 g, 1.1 mmol). After being flushed with N2, the resulting mixture was heated at 110° C. overnight, cooled to room temperature, filtered through celite and concentrated under reduced pressure to give an oil. This oil was purified by silica gel column chromatography using 30-50% EtOAc/heptane to give the titled compound as a light yellow foam (2.0 g, 77%).

1. customAfter being flushed with N2
2. temperaturecooled to room temperature
3. filtrationfiltered through celite and
4. concentrationconcentrated under reduced pressure
5. customto give an oil
6. customThis oil was purified by silica gel column chromatography

ORD record

ord-ec723c6a2cb6402ebd43409790d7e485

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993523B2