Sodium hydride → HCID 69311915, compound

Participants

Reaction Conditions

Reaction Steps

NaH (1.826 g) was added to DMF (400 mL) and cooled to 0° C. 4-(Triisopropyl-silyloxy)-1H-indole (12 g) was added portionwise at 0° C., and allowed to stir at 0° C. for 1 h. 4-Chloro-2-methylsulfanyl-pyrimidine (5.28 mL) was added dropwise, and the reaction mixture stirred at 0° C. for 4 h and then quenched with water. The aqueous layer was acidified with 1N HCl. The organic layer was extracted into DCM, and dried over sodium sulfate, filtered and the filtrate was concentrated and purified on a column with 100% hexane to 25% EtOAc/hexane to yield 1-(2-methylsulfanyl-pyrimidin-4-yl)-4-triisopropylsilanyloxy-1H-indole (11 g).

Provenance & Evidence