3-(2-(4-(Pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopent-2-enol → 3-(2-(4-(Pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopentanol

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopent-2-enol (190 mg, 0.550 mmol) in Tetrahydrofuran (10 mL) was treated with palladium, 10% wt. on activated carbon (58.5 mg, 0.055 mmol, 0.1 equiv). The reaction mixture was purged with vacuum-hydrogen cycles (3×), and stirred at 23° C. under hydrogen. After 5 h, the reaction was heated to 45° C. After 24 h, the reaction was cooled to 23° C., and filtered through celite. The filter cake was washed with tetrahydrofuran (100 mL), the filtrates combined, concentrated in vacuo, and purified by silica gel chromatography (eluant: 0.5-4% methanol/dichloromethane), affording 3-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopentanol (94 mg, 49% yield). MS (ESI, pos. ion) m/z: 348.1 (M+1). IC50 (uM) 0.010.

Provenance & Evidence