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1,1'-Carbonyldiimidazole → HCID 18005174, Verbindung

HRID 1977762
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1977762
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.[C:15]([N:22]1[CH:26]=[CH:25]N=[CH:23]1)(N1C=CN=C1)=[O:16].[Cl:27][C:28]1[CH:36]=C2[C:31](CCN2)=[CH:30][C:29]=1[CH3:37]>ClCCl.CN(C)C=O>[Cl:27][C:28]1[CH:36]=[C:23]2[C:31]([CH2:25][CH2:26][N:22]2[C:15](=[O:16])[NH:6][C:5]2[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)[CH:4]=2)=[CH:30][C:29]=1[CH3:37]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 221860806-Chloro-5-methylindolineHCID 224735854-Methyl-3-(pyridin-3-yl)aniline

Produkt 1

HCID 18005174HCID 18005174, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

4-Methyl-3-(pyrid-3-yl) aniline (0.30 g, 0.0016 mole) in dry dichloromethane (20 ml) was added, under argon, to 1,1′-carbonyldiimidazole in dry dichloromethane (10 ml) (0.30 g, 0.0018 mole) and stirred at ambient temperature for 1 hour. The solvent was removed in vacuo and the residue dissolved in dry dimethylformamide (30 ml). 6-Chloro-5-methylindoline (see WO 95/01976) (0.27 g, 0.0016 mole) in dry dimethylformamide (10 ml) was added and the mixture heated to 100° C. for 1 hour. After cooling to ambient temperature, the solvent was removed in vacuo and the residue diluted with deionised water (15 ml), extracted into dichloromethane (2×20 ml), dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 3% methanol/dichloromethane and the resulting solid recrystallised from ethyl acetate/methanol/60-80° petroleum ether to afford the title compound (0.31 g, 57%) as a cream solid (mp 202-203° C.).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dry dimethylformamide (30 ml)
  3. temperaturethe mixture heated to 100° C. for 1 hour
  4. temperatureAfter cooling to ambient temperature
  5. customthe solvent was removed in vacuo
  6. additionthe residue diluted with deionised water (15 ml)
  7. extractionextracted into dichloromethane (2×20 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel
  11. washeluting with 3% methanol/dichloromethane
  12. customthe resulting solid recrystallised from ethyl acetate/methanol/60-80° petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-97f91b8659df470c9378b039cf64a172
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06235758B1

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