Potassium Iodide → 8-(Acetoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1789204ノート

反応式

HRID 1789204 の反応式
[C:1]([O:4][CH2:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2].Cl[CH:14]([CH3:18])[C:15](=O)[CH3:16].[I-].[K+]>>[C:1]([O:4][CH2:5][C:6]1[C:7]2[N:8]([C:14]([CH3:18])=[C:15]([CH3:16])[N:12]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

参加物

4

反応物 3

HCID 4875Potassium IodideHCID 200263-Chloro-2-butanoneHCID 201888553-(Acetoxymethyl)-2-pyridinamine

生成物 1

HCID 201888548-(Acetoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridine収率 28.2%

実験手順

A mixture of 2.0 g (12 mmole) of 3-(acetoxymethyl)-2-pyridinamine, 1.7 g (17 mmole) of 3-chloro-2-butanone, and one crystal of potassium iodide was heated at 100° for 4.5 hours. The mixture was allowed to cool and was partitioned between aqueous potassium carbonate and dichloromethane. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The solid was triturated with diethyl ether and collected by filtration to yield 738 mg of 8-(acetoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridine, as confirmed by the nmr and infrared spectra and by elemental analysis. [Calcd. for C12H14N2O2 : C, 66.04; H, 6.47; N, 12.84. Found: C, 66.01; H, 6.38; N, 13.05.] A mixture of 700 mg (3.2 mmole) of 8-(acetoxymethyl)-2,3-dimethylimidazo[1,2-a]pyridine and 482 mg (3.2 mmole) of 2-mercaptobenzimidazole in 10 ml of 15% hydrogen bromide in acetic acid was heated on a steam bath. After being cooled to room temperature, the mixture was partitioned between 5% aqueous sodium hydroxide and dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated to an oil. Spinning disk chromatography on silica gel (using 1% by volume ethanol-dichloromethane as eluent) yielded 1.05 g of the title compound Structure assignment was supported by the nmr and infrared spectra.

後処理

  1. temperaturewas heated at 100° for 4.5 hours
  2. temperatureto cool
  3. customwas partitioned between aqueous potassium carbonate and dichloromethane
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid was triturated with diethyl ether
  10. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-eff051348c4b450b8fe17199751685fc
出典データセット
uspto-grants-1987_08
特許番号
US04687775

反応ノート

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