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-c8bf5106df694118a4b86ef9e3b64694

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557816B2