تفاعل #80641

معادلة التفاعل

hydroxylamine-O-sulfonic acid

3-methyl-5-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

triethylborane

sodium acetate

→

4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl) -1H-imidazol-1-yl]benzenesulfonamide

المردود 9.6%

المذيبات

THF

THF

water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe solution was stirred at room temperature for 2 hours
2. 2
   workup.STIRRINGAfter stirring at for 2 hours
3. 3
   درجة الحرارةthe mixture was heated
4. 4
   درجة الحرارةto reflux for 72 hours
5. 5
   درجة الحرارةThe reaction mixture was cooled to room temperature
6. 6
   workup.STIRRINGAfter stirring for 5 minutes
7. 7
   workup.STIRRINGthe mixture was stirred for 20 hours
8. 8
   استخلاصThe reaction mixture was extracted with ether (2×100 mL)
9. 9
   تجفيفThe ethereal layer was dried over MgSO4
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated in vacuo
12. 12
    أخرىThe crude product was purified by chromatography on silica gel (isopropanol/toluene, 5:95)

الإجراء التجريبي

To a solution of 3-methyl-5-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (Example 41) (1.9 mmol) in 25 mL of dry THF was added n-Bu4MgCl (3.8 mL of 2.0M THF solution, 7.5 mmol) slowly at 0° C. After stirring for additional 15 minutes, the solution was stirred at room temperature for 2 hours. The reaction mixture was re-cooled to 0° C. and triethylborane (9.5 mL of 1.0M THF solution, 9.5 mmol) was added. After stirring at for 2 hours, the mixture was heated to reflux for 72 hours. The reaction mixture was cooled to room temperature and treated with a solution of sodium acetate (2.3 g) in 10 mL of water. After stirring for 5 minutes, hydroxylamine-O-sulfonic acid (2.3 g) was added and the mixture was stirred for 20 hours. The reaction mixture was extracted with ether (2×100 mL). The ethereal layer was dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel (isopropanol/toluene, 5:95) to give 0.07 g of 4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl) -1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (8%): mp 242°-243° C. Anal. Calc'd. For C16H13F3N4O2S: C, 50.26, H, 3.43, N, 14.65, S, 8.39. Found: C, 50.02, H, 3.63, N, 14.26, S, 8.41.

المصدر