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Dichloromethane → Tert-butyl (5-(prop-1-en-2-yl)pyridin-3-yl)methylcarbamate

HRID 2070966
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2070966
[CH2:1](Cl)Cl.Br[C:5]1[CH:6]=[C:7]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[N:9][CH:10]=1.C(N([CH2:25][CH3:26])CC)C>C(O)(C)C.O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]=[C:25]([C:5]1[CH:6]=[C:7]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[N:9][CH:10]=1)[CH3:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 467392903-(N-BOC-aminomethyl)-5-bromopyridine

Produkt 1

HCID 86647417Tert-butyl (5-(prop-1-en-2-yl)pyridin-3-yl)methylcarbamateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel
HCID 21889133Propan-2-ol--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of potassium isopropenyl trifluoroborate (464 mg, 3.13 mmol), PdCl2(dppf).CH2Cl2 (153 mg, 0.06 mmol), tert-butyl (5-bromopyridin-3-yl)methylcarbamate (900 mg, 3.13 mmol) and triethylamine (475 mg, 4.69 mmol) in i-PrOH—H2O (2:1, 30 mL) was heated under reflux in a nitrogen atmosphere. The reaction mixture was heated at reflux for 4 h, then cooled to rt and diluted with water (40 mL) followed by extraction with diethylether. The organic layers were combined and washed with brine, dried over sodium sulfate and then filtered. The solvent was removed under vacuum, and the crude product was purified by silica gel chromatography (eluting with 45% EtOAc/hexanes) to afford tert-butyl (5-(prop-1-en-2-yl)pyridin-3-yl)methylcarbamate as a white solid in 85% yield. (5-(prop-1-en-2-yl)pyridin-3-yl)methanamine was then generated by removal of the Boc protecting group by treatment with HCl (in methanol or dioxane) or trifluoroacetic acid in dichloromethane.

Aufarbeitung

  1. temperatureunder reflux in a nitrogen atmosphere
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 4 h
  4. extractionfollowed by extraction with diethylether
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed under vacuum
  9. customthe crude product was purified by silica gel chromatography (eluting with 45% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ef7f6c239bb9468285edd60896d534dc
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299267B2

Notizen zur Reaktion

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