Potassium Carbonate → HCID 66820470, Verbindung

To a solution of 2-amino-5-bromopyridine-3-sulfonyl chloride (reagent preparation 25, step 1) (0.40 g, (1.47 mmol) in a mixture of 1,4-dioxane (8.0 mL) and water (1.0 mL) was added triphenylphosphine (1.64 g, 6.25 mmol) and the reaction mixture was stirred for 50 minutes at room temperature. Potassium carbonate (0.35 g, 2.50 mmol) was introduced, followed by 4-bromo-2-methyl-2-butanol (Tetrahedron Letters 2000, 41(38), 7337-7340) (0.31 g, 1.86 mmol) and the reaction mixture was stirred at 80° C. for 16 hours. After cooling to room temperature the reaction mixture was concentrated and the residue was partitioned between brine (50 mL) and ethyl acetate (100 mL). The organic layer was separated and washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated. Gradient flash chromatography (25% to 50% ethyl acetate in hexane) provided 4-[(2-amino-5-bromopyridin-3-yl)thio]-2-methylbutan-2-ol (0.18 g, 42%); MS (EI) for C10H15BrN2OS: 292 (MH+).

1. stirringthe reaction mixture was stirred at 80° C. for 16 hours
2. temperatureAfter cooling to room temperature the reaction mixture
3. concentrationwas concentrated
4. customthe residue was partitioned between brine (50 mL) and ethyl acetate (100 mL)
5. customThe organic layer was separated
6. washwashed with brine (50 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD-Eintrag

ord-f989ad82270747cf891fcaa21edfa931

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08648066B2