Réaction #80648

Équation de réaction

3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

n-Bu4NF

sodium acetate

hydroxylamine-O-sulfonic acid

→

3-[1-[4-[[2(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol -2-yl]pyridine

4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide

Rendement 173.5%

Solvants

THF

Water

ethyl acetate

water

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated
2. 2
   Températureto reflux for 1 hour
3. 3
   AutreThe organic phase was separated
4. 4
   Lavagewashed with saturated NaHCO3 solution, water, brine
5. 5
   Séchagedried over HgSO4
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe filtrate was concentrated
8. 8
   Autrethe residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

Mode opératoire

3-[1-[4-[[2(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol -2-yl]pyridine was prepared from Example 30 with a method similar to that described in Example 48, Step 1. To a solution of 3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (0.200 g, 0.46 mmol) in 1.0 mL of dry THF was added n-Bu4NF (1.38 mL of 1.0H THF solution, 1.38 mmol). The mixture was heated to reflux for 1 hour and cooled to room temperature. A solution of sodium acetate (0.17 g, 2.1 mmol) in 3 mL of water and hydroxylamine-O-sulfonic acid (0.26 g, 2.3 mmol) were added sequentially and the mixture was stirred for 1 hour. Water (7 mL) and ethyl acetate (7 mL) were added. The organic phase was separated and washed with saturated NaHCO3 solution, water, brine, dried over HgSO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to give 0.147 g of 4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (87%): mp(DSC) 213°-215 ° C. Anal. Calc'd. for C15H11F3N4O2S: C, 48.91; H, 3.01; N, 15.21; S, 8.71. Found: C, 48.58; H, 2.99; N, 14.87; S, 8.85.

Source