Sodium Chloride → 5-Bromo-4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo(2,3-b)pyridine

5-Bromo-1H-pyrrolo[2,3-b]pyridine 7-oxide (150 mg, 0.704 mmol) in N,N-dimethylformamide (2 mL) was heated to 50° C. and stirred with methanesulfonyl chloride (58 μL, 0.75 mmol) at 70° C. for 2 hours and allowed to cool to room temperature. After addition of saturated aqueous sodium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (2 mL), cooled to 0° C., mixed with sodium hydride (55 wt % dispersion in mineral oil, 45 mg, 1.03 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (186 μL, 1.05 mmol) and stirred at room temperature for 3 hours. After addition of saturated aqueous sodium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1 (v/v)) to give the title compound as a pale yellow oil (158 mg, yield 62%).

1. extractionthe reaction mixture was extracted with ethyl acetate
2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. dissolutionThe resulting residue was dissolved in N,N-dimethylformamide (2 mL)
5. temperaturecooled to 0° C.
6. extractionthe reaction mixture was extracted with ethyl acetate
7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1 (v/v))

ORD record

ord-f6df23fa91c54e01b7399d6791dec66b

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216999B2