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Formic Acid → HCID 15383547, Verbindung

HRID 743769
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 743769
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[C:22]([NH:23][C:24]([CH:26]3[CH2:28][CH2:27]3)=O)=[C:21]([CH3:29])[C:20](Br)=[CH:19][N:18]=2)=[CH:11][CH:10]=1)#[N:2].C(O)=O.C(N(CC)CC)C>[Pd].C1(C)C=CC=CC=1>[CH:26]1([C:24]2[N:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:1]#[N:2])=[CH:10][CH:11]=3)[C:17]3=[N:18][CH:19]=[CH:20][C:21]([CH3:29])=[C:22]3[N:23]=2)[CH2:28][CH2:27]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 15837815HCID 15837815, Verbindung

Produkt 1

HCID 15383547HCID 15383547, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

Toluene (30 ml) was added to 2.0 g (4.3 mmol) of 2-(2'-cyanobiphenyl-4-yl)methylamino-3-cyclopropanecarboxamido-5-bromo-4-methyl-pyridine, 1.0 g (21.7 mmol) of formic acid, 3.5 g (34.6 mmol) of triethylamine and 10% Pd-C (300 mg), followed by heating under reflux for 6 hours. After the reaction liquid was brought to room temperature and filtered to remove the catalyst, vacuum concentration was effected. Chloroform (100 ml) and water (50 ml) were added to the residue and the obtained mixture was caused liquid-liquid separation. The aqueous phase was further extracted with chloroform (50 ml) twice. The organic phases were combined, dried over anhydrous magnesium sulfate and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to give 1.3 g of 2-cyclopropyl-3-(2'-cyanobiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridine (yield 82%).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. customAfter the reaction liquid
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto remove
  7. concentrationthe catalyst, vacuum concentration
  8. additionChloroform (100 ml) and water (50 ml) were added to the residue
  9. customliquid-liquid separation
  10. extractionThe aqueous phase was further extracted with chloroform (50 ml) twice
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationsubjected to vacuum concentration
  13. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-81d697787de4418d8416a81dfe3b90ba
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05557002

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