반응 #88362

반응 방정식

pyridine

propane-1-sulfonyl chloride

(3-amino-2,6-difluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

dichloromethane

pyridine

propane-1-sulfonyl chloride

→

desired compound

수율 50.0%

propane-1-sulfonic acid [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-amide

수율 50.0%

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   workup.STIRRINGThe reaction is stirred at room temperature another 3 hours
3. 3
   추출extracted 3×250 mL with dichloromethane
4. 4
   세척washed with 250 mL of brine
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축the filtrate concentrated under vacuum
8. 8
   기타The resulting material is purified by silica gel column chromatography
9. 9
   세척eluting with a gradient of ethyl acetate
10. 10
    농축concentrated under vacuum

실험 절차

Into a reaction flask under nitrogen, (3-amino-2,6-difluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (7, 13.00 g, 36.9 mmol) is combined with 150 mL of dichloromethane and anhydrous pyridine (5.84 g, 73.8 mmol), and propane-1-sulfonyl chloride (8, 6.05 g, 42.5 mmol) is added. The reaction is stirred at room temperature overnight, and additional pyridine (1.46 g, 18.5 mmol) and propane-1-sulfonyl chloride (1.51 g, 10.6 mmol) are added. The reaction is stirred at room temperature another 3 hours, then diluted with 500 mL of water and extracted 3×250 mL with dichloromethane. The organic layers are combined and washed with 250 mL of brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate:hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (9, 8.41 g, 50%).

출처