Methyl iodide → 7-Chloro-2-methyl-furo[3,2-B]pyridine

In an oven-dried round bottom flask, 7-chloro-2-iodofuro[3,2-b]pyridine (0.200 g, 0.72 mmol) was dissolved in 3 mL THF and cooled to −78° C. nBuLi (0.43 ml, 1.1 mmol) was slowly added and the reaction was stirred for one hour. Meanwhile, a vial was filled with MeI and warmed to RT. Magnesium sulfate was added and the mixture was stirred for 5 minutes and filtered into another vial. Immediately from this vial, MeI (0.11 ml, 1.8 mmol) was added to the reaction which was stirred at −78° C. for 3 hours. The reaction was quenched with saturated ammonium chloride solution and warmed to RT. DCM was added, the layers were separated, and the aqueous layer was extracted twice with DCM. The combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (gradient elution 0-50% EtOAc:Hex) to afford 7-chloro-2-methylfuro[3,2-b]pyridine as a light brown oil. MS: M+H+=168.3.

1. additionwas slowly added
2. stirringthe mixture was stirred for 5 minutes
3. filtrationfiltered into another vial
4. stirringwas stirred at −78° C. for 3 hours
5. customThe reaction was quenched with saturated ammonium chloride solution
6. temperaturewarmed to RT
7. additionDCM was added
8. customthe layers were separated
9. extractionthe aqueous layer was extracted twice with DCM
10. dry with materialThe combined organic layers were dried with sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe material was purified via column chromatography (gradient elution 0-50% EtOAc:Hex)

ORD record

ord-abe65862d7ab4b1bbb57361557ecf3f7

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557816B2