Hydrogen Peroxide → 4-Chloro-5-(methylsulfonyl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Temperature

-78 °C

s-Butyllithium-hexane/cyclohexane solution (1.06 M, 0.700 mL, 0.742 mmol) was gradually added dropwise to 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.324 mmol) obtained in Reference Synthetic Exampleb 6 in tetrahydrofuran (1 mL) cooled to −78° C., and the reaction mixture was stirred at −78° C. for 30 minutes and stirred with dimethyl disulfide (30 μL, 0.33 mmol) at −78° C. for 30 minutes. After addition of 1 M aqueous sodium hydroxide, 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 ethanol (2 mL) and stirred with ammonium molybdate tetrahydrate (40 mg, 0.032 mmol) and aqueous hydrogen peroxide (30 wt %, 132 μL, 1.29 mmol) at room temperature for 5 hours. After addition of water, 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→5/1 (v/v)) to give the title compound as a pale yellow oil (61.4 mg, yield 49%).

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 ethanol (2 mL)
5. extractionthe reaction mixture was extracted with ethyl acetate
6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→5/1 (v/v))

ORD record

ord-c6210a52b2d24adeb3442514033890b3

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216999B2