Sodium Hydroxide → 4-thiazol-2-yl-1H-indole

Participants

Reaction Conditions

Reaction Steps

Palladium catalyst Pd(PPh3)4 (142 mg, 0.12 mmol) and freshly prepared aqueous sodium hydroxide (493 mg, 12.33 mmol in 6 mL of water) were added to a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (1 g, 4.11 mmol) and 2-bromothiazole (809 mg, 4.93 mmol) in THF (20 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 4 hours. It was then cooled to room temperature and ethyl acetate (300 mL) was added. The organic layer was isolated, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was triturated with dichloromethane to give 350 mg (42%) of 4-thiazol-2-yl-1H-indole as a pale yellow solid.

Provenance & Evidence