* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
n-BuLi (3 mL, 2.5 M in hexane, 1.50 equiv) was added dropwise into a solution of 2,6- dichloro-4-iodopyridine (1.40 g, 5.112 mmol, 1.00 equiv) in tetrahydrofuran (20 mL) at -78C under nitrogen. The resulting solution was stirred for 30 mm at -78C. Trimethyl borate (580 mg, 5.582 mmol, 1.10 equiv) was added at -78C and the reaction was stirred for 1 h at -78C. The resulting solution was stirred for an additional 12 h at room temperature, quenched by 1.6 g of pinacol and then AcOH (0.6 mL). The solids were filtered out and the liquid was concentrated under vacuum. This resulted in the title compound (1 g, crude) as a yellow solid.
4-(2,6-dichloropyridin-4-ylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 1h;Inert atmosphere; Reflux;
A mixture of 2,6-dichloro-4-iodopyridine (2.06 g, 7.52 mmol), tert-butyl 4- sulfanylpiperidine-l-carboxylate (1.8 ml, 8.27 mmol),4,5-Bis(diphenylphosphino)-9,9- dimethylxanthene (0.44 g, 0.75 mmol) and DIPEA (2.5 ml, 15.04 mmol) in anhydrous Dioxane (20 mL) was flushed with nitrogen for 5 minutes before Pd2(dba)3 (0.34 g, 0.38 mmol) was added and the resulting mixture was refluxed for 1 h. The reaction was cooled and partitioned between DCM (100 mL) and saturated aq. ammonium chloride solution (100 mL). The aqueous was extracted with DCM (80 mL) and the combined organics were washed with water (80 mL), brine (80 mL) and dried (hydrophobic frit). The crude material was purified by flash chromatography, eluting with EtOAc (0 - 30 %) in heptane to give the title compound as a pale yellow oil (2.37 g, 88 %). MS: m/z = 362.95 (M+H)+.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
