Methyl iodide → HCID 22143505, compound

Temperature

-78 °C

A solution of n-butyllithium (0.71 ml, 1.77 mmol) in THF (20.0 mL) was cooled to −78° C. and 7-chlorothieno[3,2-b]pyridine (200 mg, 1.18 mmol) was added dropwise. The mixture stirred at −78° C. for 1 h to afford a yellow suspension. A solution of iodomethane (0.22 ml, 3.54 mmol) in THF (1.0 mL) was added dropwise via syringe, and the mixture stirred at −78° C. for 3 h.; LCMS showed completion of the reaction. The reaction was quenched with water and warmed to RT. The layers were separated, and the aqueous phase was extracted with DCM. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a tan solid. This material was purified via column chromatography (RediSep 40 g column, gradient elution with 10-50% ethyl acetate-hexane) to afford 7-chloro-2-methylthieno[3,2-b]pyridine as white solid. MS [M+H]=184.1; Calc'd for C8H6ClNS: 183.7.

1. customto afford a yellow suspension
2. stirringthe mixture stirred at −78° C. for 3 h.
3. customcompletion of the reaction
4. customThe reaction was quenched with water
5. temperaturewarmed to RT
6. customThe layers were separated
7. extractionthe aqueous phase was extracted with DCM
8. washThe combined organic phases were washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customto afford a tan solid
13. customThis material was purified via column chromatography (RediSep 40 g column, gradient elution with 10-50% ethyl acetate-hexane)

ORD record

ord-c0f5e11358f645b59aa05eb6bbfa04bb

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07776857B2