2-Amino-3-benzyloxypyridine → 3-(2-Methyl-2-nitropropyl)-8-(phenylmethoxy)imidazo[1,2-a]pyridine

HRID 914946노트

반응식

HRID 914946 반응식
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH:17]([CH2:20][C:21]([CH3:26])([N+:23]([O-:25])=[O:24])[CH3:22])[CH:18]=O>C(O)C>[CH3:22][C:21]([N+:23]([O-:25])=[O:24])([CH3:26])[CH2:20][C:17]1[N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:2]2=[N:1][CH:18]=1

참가 물질

4

반응물 2

HCID 903342-Amino-3-benzyloxypyridineHCID 220385582-Bromo-4-methyl4-nitropentanal

생성물 1

HCID 220385573-(2-Methyl-2-nitropropyl)-8-(phenylmethoxy)imidazo[1,2-a]pyridine수율 64.4%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-amino-3-benzyloxypyridine (2.7 g, 13.5 mmol) and 2-bromo-4-methyl-4-nitropentanal (3.0 g, 13.5 mmol) in ethanol (20 ml) is heated at 100° C. overnight. The solvent is removed under reduced pressure and the residue is treated with saturated aqueous NaHCO3 solution. The aqueous mixture is extracted two times with ethyl acetate. The combined organic extracts are dried over magnesium sulfate and concentrated in vacuo. The residue is chromatographed (silica gel, dichloromethane/ethanol 9:1) to give 2.83 g of 3-(2-methyl-2-nitropropyl)-8-(phenylmethoxy)imidazo[1,2-a]pyridine (64%).

후처리

  1. customThe solvent is removed under reduced pressure
  2. additionthe residue is treated with saturated aqueous NaHCO3 solution
  3. extractionThe aqueous mixture is extracted two times with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed (silica gel, dichloromethane/ethanol 9:1)

출처 및 근거

ORD 기록
ord-4bb5992a8b584ae39367338add6887e4
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265127B2

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