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

Participants

Reaction Conditions

Reaction Steps

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]−.

Provenance & Evidence