1-Phenethylamine, (-)- → (S)-[4-(3-Chloro-indazol-1-yl)-pyridin-2-yl]-(1-phenyl-ethyl)-amine

Temperature

70 °C

To a solution of 3-chloro-1-(2-chloro-pyridin-4-yl)-1H-indazole (0.29 g, 1.1 mmol) in toluene (6 mL) under nitrogen were added palladium acetate (0.025 g, 0.11 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.069 g, 0.1 mmol), and (S)-(−)-α-methylbenzylamine (0.18 mL, 1.38 mmol), followed by sodium t-butoxide (0.3 g, 3.1 mmol). The resulting mixture was heated at 70° C. for 1 h, during which TLC and HPLC indicated completion of reaction. After cooling to room temperature, the reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate and brine and dried over MgSO4. Flash chromatography of the crude product mixture with 25:10:65, 35:10:55, and 50:10:40 EtOAc-CH2Cl2-hexane gave the title compound as a tan colored solid. MS (ES+): 349.3 [M+H]+, 347.1 [M−H]−.

1. customcompletion of reaction
2. temperatureAfter cooling to room temperature
3. washwashed with saturated sodium bicarbonate and brine
4. dry with materialdried over MgSO4

ORD record

ord-dbb28ce2443f43978b1f7bf7b806ec71

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582631B2