Potassium Phosphate, Tribasic → 7-Chloro-2-cyclopropylfuro[3,2-b]pyridine

Temperature

100 °C

7-Chloro-2-iodofuro[3,2-b]pyridine (0.130 g, 0.47 mmol), cyclopropylboronic acid (0.080 g, 0.93 mmol), and tricyclohexylphosphine (0.026 g, 0.093 mmol) were dissolved in 3 mL toluene and 1 mL water. Potassium phosphate (0.30 g, 1.4 mmol) was added followed by PdOAc2 (0.010 g, 0.047 mmol), the reaction was flushed with argon, and the reaction stirred at 100° C. for 48 h. The reaction was cooled to RT and partitioned between DCM and water. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were dried with sodium sulfate, filtered, and concentrated. The crude material was purified via column chromatography (gradient elution 0-50% EtOAc:Hex) to afford 7-chloro-2-cyclopropylfuro[3,2-b]pyridine as an orange oil. MS: M+H+=194.4.

1. customthe reaction was flushed with argon
2. temperatureThe reaction was cooled to RT
3. custompartitioned between DCM and water
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with DCM
6. dry with materialThe combined organic layers were dried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude material was purified via column chromatography (gradient elution 0-50% EtOAc:Hex)

ORD record

ord-306d0a10b49f417b82208ed42912102c

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557816B2