Reacción #328250

Ecuación de reacción

4-bromo-2-methyl-2-butanol

2-amino-5-bromopyridine-3-sulfonyl chloride

triphenylphosphine

Potassium carbonate

→

4-[(2-amino-5-bromopyridin-3-yl)thio]-2-methylbutan-2-ol

Rendimiento 42.0%

Disolventes

1,4-dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture was stirred at 80° C. for 16 hours
2. 2
   TemperaturaAfter cooling to room temperature the reaction mixture
3. 3
   Concentraciónwas concentrated
4. 4
   Otrothe residue was partitioned between brine (50 mL) and ethyl acetate (100 mL)
5. 5
   OtroThe organic layer was separated
6. 6
   Lavadowashed with brine (50 mL)
7. 7
   Secadodried over sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated

Procedimiento

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+).

Fuente