Tetrahydrofuran → HCID 51353923, compound

Temperature

70 °C

A round-bottomed flask was charged with 2-chloro-4-iodopyridine (600 mg, 2.5 mmol), thiophen-2-ylboronic acid (385 mg, 3.0 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (176 mg, 0.251 mmol), THF (9 mL) and 2M aqueous sodium carbonate (3.0 mL, 6.0 mmol). The reaction mixture was stirred at 70° C. overnight. The reaction mixture was cooled to room temperature then diluted with 20 mL water and extracted with 100 mL EtOAc (2×). The combined organic layers were washed with 20 mL water and 20 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on ˜2 g SiO2 and chromatographed over 24 g SiO2 with EtOAc/hexanes (gradient: 0-10% EtOAc). All fractions containing product were combined and concentrated to give 430 mg (88%) of 2-chloro-4-thiophen-2-yl-pyridine as a light yellow solid.

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionextracted with 100 mL EtOAc (2×)
3. washThe combined organic layers were washed with 20 mL water and 20 mL brine
4. dry with materialthen dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was absorbed on ˜2 g SiO2
8. customchromatographed over 24 g SiO2 with EtOAc/hexanes (gradient: 0-10% EtOAc)
9. additionAll fractions containing product
10. concentrationconcentrated

ORD record

ord-6a0ad571fe0b48ac9e7027f6843d28a5

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2