Sodium Iodide → HCID 57516632, compound

Temperature

80 °C

A 20 mL microwave vial was charged with 2-chloro-4-thiophen-2-yl-pyridine (428 mg, 2.19 mmol), sodium iodide (3.28 g, 21.9 mmol) and acetonitrile (3.5 mL). Acetyl chloride (0.24 mL, 3.4 mmol) was added and the vial was flushed with Argon and closed. The reaction mixture was stirred at 80° C. overnight. The reaction mixture was cooled to room temperature and quenched with 10 mL saturated Na2CO3 solution then extracted with 50 mL dichloromethane. The organic layer was washed with 10 mL 10% Na2S2O3 solution. The aqueous layers were extracted twice with 50 mL dichloromethane. The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over 24 g SiO2 with EtOAc/hexanes (gradient: 0-10% EtOAc). All fractions containing product were combined and concentrated to afford 563 mg (90%) of 2-iodo-4-thiophen-2-yl-pyridine as a light yellow solid.

1. customthe vial was flushed with Argon
2. customclosed
3. temperatureThe reaction mixture was cooled to room temperature
4. customquenched with 10 mL saturated Na2CO3 solution
5. extractionthen extracted with 50 mL dichloromethane
6. washThe organic layer was washed with 10 mL 10% Na2S2O3 solution
7. extractionThe aqueous layers were extracted twice with 50 mL dichloromethane
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was chromatographed over 24 g SiO2 with EtOAc/hexanes (gradient: 0-10% EtOAc)
12. additionAll fractions containing product
13. concentrationconcentrated

ORD record

ord-99c1e70398884ae2b4b6c897f923d308

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2