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

HRID 1377474
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HRID 1377474 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 14798Sodium Hydroxide촉매
HCID 6342
Acetonitrile
용매
2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ec75cfac7f3c418489cf5a794ba7da4c
출처 데이터셋
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05665730

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