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

HRID 1271544ノート

反応式

HRID 1271544 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-aecf931daf5b452495cf6d332b9d36c6
出典データセット
uspto-grants-2007_04
特許番号
US07205407B2

反応ノート

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