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Potassium Fluoride → 8-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1377476
노트
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HRID 1377476 반응식
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:7]=1[CH2:8]Cl)=[O:4].[OH:15][C:16]1[C:17]2[N:18]([C:22]([CH3:26])=[C:23]([CH3:25])[N:24]=2)[CH:19]=[CH:20][CH:21]=1.[F-].[K+]>C(#N)C>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:7]=1[CH2:8][O:15][C:16]1[C:17]2[N:18]([C:22]([CH3:26])=[C:23]([CH3:25])[N:24]=2)[CH:19]=[CH:20][CH:21]=1)=[O:4]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 522689Potassium FluorideHCID 143684802-Methyl-6-methoxycarbonylaminobenzyl chlorideHCID 224679492,3-Dimethylimidazo[1,2-a]pyridin-8-ol

생성물 1

HCID 232872868-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2,3-dimethylimidazo[1,2-a]pyridine

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

반응 조건

온도
70 °C

실험 절차

A solution of 9.5 g of 2-methoxycarbonylamino-6-methylbenzyl chloride in 150 ml of dry acetonitrile is added dropwise at RT to a suspension of 7.2 g of 8-hydroxy-2,3-dimethylimidazo[1,2-a]pyridine in 130 ml of dry acetonitrile, to which 8 g of commercial potassium fluoride (50% by weight) in kieselguhr (for example Celite®) has been added. The mixture is heated at 70° C. for 9 h. After cooling to RT, the mixture is poured into 1 l of ice-water and extracted three times with ethyl acetate. The collected organic phases are washed with distilled water and dried over sodium sulfate. After stripping off the organic solvent in vacuo, the precipitating residue is filtered off, washed with a little ethyl acetate and ether and dried. After recrystallization from isopropanol, 2.2 g of the title compound of m.p. 176°-177° C. are obtained.

후처리

  1. additionhas been added
  2. temperatureAfter cooling to RT
  3. extractionextracted three times with ethyl acetate
  4. washThe collected organic phases are washed with distilled water
  5. dry with materialdried over sodium sulfate
  6. filtrationthe precipitating residue is filtered off
  7. washwashed with a little ethyl acetate and ether
  8. customdried
  9. customAfter recrystallization from isopropanol, 2.2 g of the title compound of m.p. 176°-177° C.
  10. customare obtained

출처 및 근거

ORD 기록
ord-05cf1de09de7446cbd84e3d36fb78660
출처 데이터셋
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05665730

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