Sodium hydride → HCID 59398559, compound

Participants

Reaction Steps

4-Chloro-1H-pyrrolo[2,3-b]pyridine (20 g, 131 mmol) was dissolved in hydrous DMF (200 mL), and sodium hydride (60%, 6.0 g, 150 mmol) was added thereto. The resulting mixture was stirred under ice-cooling for 30 minutes, and then benzyloxymethyl chloride (26.8 g, 171 mmol) was added thereto. The resulting mixture was stirred under ice-cooling for 1 hour and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate (300 mL) and saturated brine (200 mL). The aqueous layer was further extracted with ethyl acetate (300 mL). The combined organic layer was washed with saturated brine, dried, and concentrated. The residue was purified by silica-gel column chromatography (manufactured by Fuji Silysia, BW300 1500CC, n-hexane:EtOAc=4:1) to give 34 g of 1-benzyloxymethyl-4-chloro-1H-pyrrolo[2,3-b]pyridine as a light-yellow syrup (yield: 95%).

Provenance & Evidence