Sodium Carbonate → 4-(4'-Chlorobiphenyl-4-yloxy)-1-pyridin-3-yl-pentan-3-ol

Temperatur

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 (0.20 g, Example 11)), 4-chloro-iodobenzene (0.24 g), 2M aqueous sodium carbonate (0.5 ml) and tetrakis(triphenylphosphine)palladium (0) (0.1 g) in toluene (4 ml) and ethanol (1 ml). The reaction mixture 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 the suspension was stirred at room temperature for 3 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give a gum, from which the oxalate salt was made (0.11 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
7. customto give a gum

ORD-Eintrag

ord-92b59a4f959849e1a50f7c4069bcf7a7

Quelldatensatz

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06300352B1