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3-Pyridinecarboxaldehyde → Benzyl (E)-3-[2-methyl-3-(3-pyridylmethyl)-1H-indol-4-yl]-2-propenoate

HRID 1600175
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1600175
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH:7]=[CH:6][CH:5]=2.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=O)[CH:24]=1.C([SiH](CC)CC)C>ClCCl.FC(F)(F)C(O)=O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:29][C:25]1[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=1)=[C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH:7]=[CH:6][CH:5]=2
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Komponenten

6

Edukt 3

HCID 103713-PyridinecarboxaldehydeHCID 12052TriethylsilaneHCID 86752481Benzyl (E)-3-(2-methyl-1H-indol-4-yl)-2-propenoate

Produkt 1

HCID 86752482Benzyl (E)-3-[2-methyl-3-(3-pyridylmethyl)-1H-indol-4-yl]-2-propenoateAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344Dichloromethane
Lösungsmittel
HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of benzyl (E)-3-[2-methyl-1H-indol-4-yl]-2-propenoate (4.75 g) and pyridine-3-carboxaldehyde (2.10 g) in dry dichloromethane (45 ml) was added dropwise to a stirred solution of triethylsilane (7.82 ml) in trifluoroacetic acid (40 ml) at 0° C. The solution was stirred, allowing the temperature to rise to room temperature, for 45 minutes and then evaporated. The residue was partitioned between dichloromethane and dilute aqueous ammonia solution. The aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with water and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel. Elution with dichloromethane gave impurity,and further elution with dichloromethane/methanol (19:1) gave pure product.The product fractions were evaporated and the residue was triturated with ether to give the title compound (2.19 g), m.p. 180°-182° C., Rf. 0.35(SS1).

Aufarbeitung

  1. customevaporated
  2. customThe residue was partitioned between dichloromethane and dilute aqueous ammonia solution
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washthe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed on silica gel
  8. washElution with dichloromethane
  9. customgave
  10. washimpurity,and further elution with dichloromethane/methanol (19:1)
  11. customgave pure product.The product fractions
  12. customwere evaporated
  13. customthe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-d93c3fe558dd43198942a8b39f2c911c
Quelldatensatz
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05744488

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