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Potassium Fluoride → 3-Formyl-8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 1377474
ノート
印刷プレビュー

反応式

HRID 1377474 の反応式
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2].[F-].[K+].[CH3:16][O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23]Br)=[O:19]>C(#N)C.[OH-].[Na+]>[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:23][C:22]3[C:25]([CH3:29])=[CH:26][CH:27]=[CH:28][C:21]=3[NH:20][C:18]([O:17][CH3:16])=[O:19])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 522689Potassium FluorideHCID 22914806HCID 22914806、化合物HCID 232941873-Formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine

生成物 1

HCID 229148053-Formyl-8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridine収率 64.9%

試薬・触媒・溶媒 2

HCID 14798Sodium Hydroxide触媒
HCID 6342
Acetonitrile
溶媒
2 回

実験手順

2.6 g of 3-formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine are dissolved in 50 ml of dry acetonitrile with exclusion of moisture at 50° C. and, after cooling to RT, 2.8 g of commercial potassium fluoride (50% by weight) on kieselguhr (for example Celite®) are added. A solution of 3.6 g of 2-methoxycarbonylamino-6-methylbenzyl bromide in 50 ml of dry acetonitrile is added dropwise, and the mixture is heated at 70° C. for 6 h. After cooling to RT, the mixture is poured into ice-water, adjusted to pH 9 with a few drops of 6N sodium hydroxide solution and extracted with ethyl acetate. The collected organic phases are washed with water and dried over sodium sulfate. Stripping off the solvent in vacuo and stirring in a little cold methanol result in 3.2 g of the title compound of m.p. 196°-198° C.

後処理

  1. temperaturethe mixture is heated at 70° C. for 6 h
  2. temperatureAfter cooling to RT
  3. extractionextracted with ethyl acetate
  4. washThe collected organic phases are washed with water
  5. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-ec75cfac7f3c418489cf5a794ba7da4c
出典データセット
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05665730

反応ノート

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