반응 #169768

반응 방정식

CaCl2

2-Chloro-3-methyl-3H-imidazo[4,5-b]pyridine

1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

NaH

HCl

→

1-ethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

수율 58.0%

용매

DMF

반응 조건

후처리

1. 1
   추출extracted with EtOAc
2. 2
   기타The organic layer was separated
3. 3
   세척washed with water and brine
4. 4
   건조dried over MgSO4
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane)

실험 절차

2-Chloro-3-methyl-3H-imidazo[4,5-b]pyridine (150 mg) was added to a solution of 1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (228 mg) and NaH (39.4 mg) in DMF (2 mL) at 100° C. The mixture was stirred at 180° C. under a dry atmosphere (CaCl2 tube) for 1 h. The mixture was neutralized with 1N HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane) to give 1-ethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (200 mg) as white crystals.

출처