Iodoethane → 3-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 82627노트

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HRID 82627 반응식
I[CH2:2][CH3:3].[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][C:26]([CH3:27])=[C:21]3[NH:20][C:19]2=[O:28])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][C:26]([CH3:27])=[C:21]3[N:20]([CH2:2][CH3:3])[C:19]2=[O:28])=[CH:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 585772463-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

생성물 1

HCID 585773813-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

Iodoethane (0.289 mL) was added to a mixture of 3-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (998 mg) and cesium carbonate (1.96 g) in DMF (10 mL) at room temperature. The mixture was stirred at 50° C. for 4 h. The mixture was diluted with water at room temperature and extracted with AcOEt. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 15%-30% AcOEt in hexane) to give 3-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (801 mg) as an off-white solid.

후처리

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, eluted with 15%-30% AcOEt in hexane)

출처 및 근거

ORD 기록
ord-5f0ac882014f4093b2524f22a57e8ba7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846713B2

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