Sodium Carbonate → (3R,4S)-4-[3'-(2-Dimethylaminoethyl)biphenyl-4-yloxy]-1-pyridin-3-yl-pentan-3-ol

Temperature

100 °C

Prepared according to the method described in Example 12b) from (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid (0.2 g, Example 11), [2-(3-bromophenyl)ethyl]dimethylamine hydrochloride (0.21 g, Example 27a)), aqueous sodium carbonate (2M, 0.82 ml) and tertakistriphenylphosphine palladium (0) (0.1 g) in toluene (5 ml) and ethanol (2 ml). The reaction was heated at 100° C. for 4 hours. After cooling, the solution was concentrated under reduced pressure. Concentrated hydrochloric acid (1 ml) was added to a solution of the residue in methanol (5 ml) and stirred at room temperature for 2 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as an oil (0.07 g).

1. customPrepared
2. temperatureAfter cooling
3. concentrationthe solution was concentrated under reduced pressure
4. additionConcentrated hydrochloric acid (1 ml) was added to a solution of the residue in methanol (5 ml)
5. customAfter work up, the residue was purified by normal-phase HPLC
6. washeluting with a gradient of 0-25% ethanol in dichloromethane

ORD record

ord-2854a5807d2948f79424758aee06ed73

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06300352B1