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4-Methylpyridine → 1-(3-Dibenzylamino-2,6-difluoro-phenyl)-2-pyridin-4-yl-ethanone

HRID 45843
노트
인쇄 미리보기

반응식

HRID 45843 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C([O:25][C:26](=O)[C:27]1[C:32]([F:33])=[CH:31][CH:30]=[C:29]([N:34]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:28]=1[F:49])C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH2:42]([N:34]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:29]1[C:28]([F:49])=[C:27]([C:26](=[O:25])[CH2:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:32]([F:33])=[CH:31][CH:30]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 79634-Methylpyridine2회HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 584771183-Dibenzylamino-2,6-difluoro-benzoic acid benzyl ester

생성물 1

HCID 584771201-(3-Dibenzylamino-2,6-difluoro-phenyl)-2-pyridin-4-yl-ethanone수율 50%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
3회

실험 절차

To 4-methyl-pyridine (806 4, 8.33 mmol) in anhydrous tetrahydrofuran (35 mL) was added at 0° C. sodium hexamethyldisilazide 1 M in tetrahydrofuran (16.66 mL, 16.66 mmol) and the reaction was stirred for 20 minutes. 3-Dibenzylamino-2,6-difluoro-benzoic acid benzyl ester (3.691 g, 8.33 mmol) was dissolved in tetrahydrofuran (5 mL) and added dropwise to the solution with 4-methyl-pyridine, the reaction was stirred at 0° C. for one hour. The reaction was poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtrate and concentrated under reduced pressure. The crude was purified by silica gel column chromatography eluting with ethyl acetate 30% in hexane to give the title compound (1.775 g, 50%).

후처리

  1. stirringthe reaction was stirred at 0° C. for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate, filtrate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by silica gel column chromatography
  7. washeluting with ethyl acetate 30% in hexane

출처 및 근거

ORD 기록
ord-be60a6c0d40247b9b655f8894445b6ce
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541575B2

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