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Ethanol → 3-Fluoro-4-(isoquinolin-5-yl)benzenamine

HRID 2356366
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2356366
Br[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[F:9].[CH:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[C:14]=2[CH:13]=[CH:12][N:11]=1.CCO.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[F:9][C:3]1[CH:4]=[C:5]([NH2:8])[CH:6]=[CH:7][C:2]=1[C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[CH:13]=[CH:12][N:11]=[CH:10]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 599474Isoquinoline-5-boronic acidHCID 8218484-Bromo-3-fluoroaniline

Produkt 1

HCID 593839363-Fluoro-4-(isoquinolin-5-yl)benzenamineAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Bromo-3-fluorobenzenamine (2.51 g, 13 mmol) and 5-isoquinolineboronic acid (4.23 g, 24 mmol) were suspended in toluene (35 ml) and EtOH (35 ml) and tetrakis(triphenylphosphine)palladium (812 mg, 0.70 mmol) was added, followed by 10% aqueous sodium carbonate (40 ml). The flask was fitted with a reflux condenser and placed in a preheated oil bath (110 C) and stirred under nitrogen for 4 hours. The reaction was then cooled to room temperature, partially concentrated, and diluted with water. The aqueous phase was extracted with DCM, and the organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on silica gel (50:1->30:1->20:1 DCM/MeOH). The fractions with product were collected, concentrated, and washed with DCM and hexanes. The remaining solid was dried under high vacuum to afford the desired 3-fluoro-4-(isoquinolin-5-yl)benzenamine (2.568 g, 10.78 mmol, 94% purity, 82% yield). MS (ESI pos. ion) m/z: 497 (MH+). Calc'd exact mass for C15H11FN2: 239. 1H NMR (400 MHz, CDCl3): 9.30 (s, 1H), 8.50 (dd, J=6.0 Hz, 2.0 Hz, 1H), 8.02-7.96 (m, 1H), 7.68-7.63 (m, 2H), 7.58-7.54 (m, 1H), 7.16 (dt, J=8.0 Hz, 2.0 Hz, 1H), 6.61 (dt, J=8.0 Hz, 2.0 Hz, 1H), 6.56 (dt, J=11.5 Hz, 2.0 Hz, 1H), 3.93 (br s, 2H).

Aufarbeitung

  1. customThe flask was fitted with a reflux condenser
  2. customplaced in a preheated oil bath
  3. concentrationpartially concentrated
  4. additiondiluted with water
  5. extractionThe aqueous phase was extracted with DCM
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on silica gel (50:1->30:1->20:1 DCM/MeOH)
  10. customThe fractions with product were collected
  11. concentrationconcentrated
  12. washwashed with DCM and hexanes
  13. customThe remaining solid was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-85f8a1757b014981b11a6044769be523
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07759344B2

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