Bromine → HCID 68664063, compound

To a solution of ethyl furo[3,2-b]pyridine-5-carboxylate (0.30 g, 1.57 mmol) in dichloromethane (5 mL) was added dropwise bromine (7.82 mL, 157 mmol) at room temperature, and the resulting mixture was stirred for 3.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (5 mL). To this solution was added dropwise a 1 M potassium hydroxide ethanol solution (10 mL) at 0° C., and the resulting mixture was stirred at room temperature for 5 min. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=17/3-1/1) to give the title compound (0.15 g, yield 36%) as colorless crystals.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in tetrahydrofuran (5 mL)
3. additionTo this solution was added dropwise a 1 M potassium hydroxide ethanol solution (10 mL) at 0° C.
4. stirringthe resulting mixture was stirred at room temperature for 5 min
5. additionThe reaction mixture was diluted with ethyl acetate
6. washwashed with water and saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=17/3-1/1)

ORD record

ord-53b9618b42744c33a7a2d8ce579f3462

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492378B2