Sodium Hydroxide → 4-(Pyridin-4-yl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

Palladium catalyst Pd(PPh3)4 (1.00 g, 0.87 mmol) and freshly prepared aqueous sodium hydroxide (4.63 g, 115.9 mmol in 42 mL water) were added to a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (7.03 g, 28.9 mmol) and 4-bromopyridine hydrochloride (5.68 g, 29.2 mmol) in THF (98 mL). The system was degassed and then purged three times with nitrogen. The mixture was stirred under nitrogen at 70° C. in an oil bath for 6 hours. It was then cooled to room temperature and ethyl acetate (400 mL) added. The organic layer was isolated, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was triturated with dichloromethane to give 5.1 g (91%) of 4-pyridin-4-yl-1H-indole.

Provenance & Evidence