Reaktion #166170

Reaktionsgleichung

potassium phosphate

phosphine

methanesulfonamide

p-methylbenzene nonaflate

t-Amyl alcohol

→

N-p-tolylmethanesulfonamide

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar
2. 2
   TemperaturAfter cooling to room temperature
3. 3
   SonstigeThe vial was sealed with a crimp top
4. 4
   Sonstigeplaced in a heating block at 80° C
5. 5
   workup.WAITAfter 16 hours
6. 6
   Temperaturthe reaction was cooled to room temperature
7. 7
   Filtrationfiltered through a pad of diatomaceous earth
8. 8
   WaschenThe vial was rinsed with CH2Cl2 (2×2 mL)
9. 9
   Waschenthe filter cake was washed with CH2Cl2 (2×2 mL)
10. 10
    SonstigeThe filtrate was transferred to a tared flask
11. 11
    Einengenconcentrated on a rotary evaporator
12. 12
    Sonstigeto furnish an orange oil
13. 13
    EinengenThe crude concentrate
14. 14
    workup.ALIQUOTwas sampled for a wt % analysis
15. 15
    SonstigePurified material could be isolated as an off-white solid by silica gel flash column chromatography (30 g silica gel, gradient from 85:15 to 70:30 heptane:ethyl acetate) (literature reference: Shekhar S, et al. J. Org. Chem. 2011; 76: 4552-4563.)

Vorschrift

In a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar was charged with potassium phosphate (71.6 mg, 0.337 mmol, 1.1 equivalents), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (2.8 mg, 0.00307 mmol, 0.01 equivalents) and phosphine ligand (0.00736 mmol, 0.024 equivalents). t-Amyl alcohol (1.1 mL) was syringed into the vial and the mixture was stirred for 30 minutes at 80° C. After cooling to room temperature, methanesulfonamide (35.0 mg, 0.368 mmol, 1.2 equivalents) and p-methylbenzene nonaflate (100 mg, 0.307 mmol, 1 equivalent) were added to the reaction solution. The vial was sealed with a crimp top and placed in a heating block at 80° C. After 16 hours, the reaction was cooled to room temperature and brought out of the glovebox. The reaction solution was diluted with CH2Cl2 (2 mL) and filtered through a pad of diatomaceous earth. The vial was rinsed with CH2Cl2 (2×2 mL), then the filter cake was washed with CH2Cl2 (2×2 mL). The filtrate was transferred to a tared flask and concentrated on a rotary evaporator to furnish an orange oil. The crude concentrate was sampled for a wt % analysis. Purified material could be isolated as an off-white solid by silica gel flash column chromatography (30 g silica gel, gradient from 85:15 to 70:30 heptane:ethyl acetate) (literature reference: Shekhar S, et al. J. Org. Chem. 2011; 76: 4552-4563.). 1H NMR (400 MHz, CDCl3) δ ppm 7.22-7.07 (m, 4H), 6.57 (br s, 1H), 2.99 (s, 3H), 2.34 (s, 3H).

Quelle