HCID 66815517, compound → HCID 66817286, compound

Temperature

0 °C

Reagent A (2.85 mL, 3.709 mmol) was added dropwise to a solution of 4-bromo-3,3-difluoro-1,3-dihydro-indol-2-one (400 mg, 1.61 mmol) in tetrahydrofuran (8.1 mL) at 0° C. The mixture was stirred at 0° C. for 3.5 hours and at room temperature for 16 hours. Further, Reagent A (3.0 mL) was added to the reaction mixture, followed by stirring at room temperature for three hours. The reaction mixture was quenched with 3 M HCl (4.8 mL) and then extracted with ethyl acetate (×2). The organic layers were combined and sequentially washed with water and saturated brine, and then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4-bromo-3-fluoro-1H-indole as a yellow oil (132 mg, 38%).

1. stirringby stirring at room temperature for three hours
2. customThe reaction mixture was quenched with 3 M HCl (4.8 mL)
3. extractionextracted with ethyl acetate (×2)
4. washsequentially washed with water and saturated brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-2c95b3339501469a908bb4ca4aed771b

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2