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Pyridine → (E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzoyl]amino]pyridin-3-yl]acrylate

HRID 2265083
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인쇄 미리보기

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HRID 2265083 반응식
[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)[C:6]([OH:8])=O.N1C=CC=CC=1.[NH2:24][C:25]1[N:30]=[CH:29][C:28]([CH:31]=[CH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:26]=1.P(Cl)(Cl)(Cl)=O>C(#N)C.C(OCC)(=O)C.O>[CH3:16][Si:2]([CH3:1])([CH3:17])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)[C:6]([NH:24][C:25]1[N:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:26]=1)=[O:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 146056473,5-Bis(trimethylsilyl)benzoic acid2회HCID 53409341Ethyl 3-(6-aminopyridine-3-yl)acrylate

생성물 1

HCID 86644273(E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzoyl]amino]pyridin-3-yl]acrylate수율 20%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매

실험 절차

3,5-Bis(trimethylsilyl)benzoic acid (hereinafter referred to as “BTMB”; 700 mg) was suspended in acetonitrile (5.25 ml) in a nitrogen atmosphere. Pyridine (0.212 ml) and Compound 1a (603 mg) were added to the suspension, and phosphorus oxychloride (0.131 ml) was added dropwise under ice-cooling. The mixture was stirred while refluxing under heating for 3.5 hours. After the reaction mixture was allowed to cool, water and ethyl acetate were added thereto. The organic layer was washed three times with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by neutral silica gel column chromatography (5% ethyl acetate/n-hexane) to obtain Compound 1b (232 mg, 20%) as a white foam.

후처리

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. temperaturewhile refluxing
  4. temperatureunder heating for 3.5 hours
  5. temperatureto cool
  6. washThe organic layer was washed three times with water
  7. dry with materialonce with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by neutral silica gel column chromatography (5% ethyl acetate/n-hexane)

출처 및 근거

ORD 기록
ord-cf62d2e8f9544323a2b440b5956b3cc9
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07855300B2

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