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Ethanol → (4-(Pyridazin-4-yl)phenyl)methanamine

HRID 711215
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 711215
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][N:16]=[N:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N:15]1[CH:14]=[CH:13][C:18]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][NH2:1])=[CH:4][CH:5]=2)=[CH:17][N:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734312(4-(Aminomethyl)phenyl)boronic acidHCID 178889274-Bromopyridazine

Produkt 1

HCID 67208670(4-(Pyridazin-4-yl)phenyl)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a sealed tube was added 4-(aminomethyl)phenylboronic acid 1-1 (1.87 g, 10 mmol), 4-bromopyridazine 1-2 (1.58 g, 10 mmol), Pd(PPh3)4 (230 mg, 0.2 mmol), saturated Na2CO3 (15 mL), ethanol (15 mL) and toluene (45 mL). The reaction was heated to 110° C. and stirred for 2 hours. The reaction was cooled down to room temperature. The solvent was removed by rotary evaporation. The residue was dissolved in 10% methanol in DCM. The salt was removed by filtration. The filtrate was dried. The crude product was purified by silica-gel flash chromatography, eluted with 10% methanol in DCM to give (4-(pyridazin-4-yl)phenyl)methanamine 1-3 as off-white solid. MS m/z 186.2 (M+1).

Aufarbeitung

  1. temperatureThe reaction was cooled down to room temperature
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionThe residue was dissolved in 10% methanol in DCM
  4. customThe salt was removed by filtration
  5. customThe filtrate was dried
  6. customThe crude product was purified by silica-gel flash chromatography
  7. washeluted with 10% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-e5ca96c5f27c441692b3f8858e3d87f7
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181235B2

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