tert-Butyl mercaptan → HCID 131734345, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-4-chloro-7-fluoroquinoline/6-bromo-4-chloro-5-fluoroquinoline (20.35 g, 78 mmol), 2-methylpropane-2-thiol (9.68 ml, 86 mmol), sodium Na2CO3 (24.84 g, 234 mmol), Pd2dba3 (7.15 g, 7.81 mmol), and Xantphos (4.52 g, 7.81 mmol) in 1,4-Dioxane (300 ml) was stirred under nitrogen at 95° C. overnight. Cooled to RT and concentrated. Dissolved resulting material into DCM/water, and separated the layers. Extracted aqueous layer with DCM. The combined organic layers were concentrated. The crude sample was purified via Isco normal phase chromatography (330 g column, 0% -15%, E/H) to yield 6-(tert-butylthio)-4-chloro-7-fluoroquinoline/6-(tert-butylthio)-4-chloro-5-fluoroquinoline (˜20.5 g) as a yellow solid that still contained dba. MS: m/z: 270.0 [M+H]+. This sample was a mixture of regioisomers that was used as is for next step.

Provenance & Evidence