StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Pyridine → 7-bromo-5-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole

HRID 2421230
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2421230
[Br:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[F:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1C=CC=CC=1.B(O)O>ClCCl.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]2[C:10]=1[N:9]([C:23]1[CH:24]=[CH:25][C:26]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[C:21]([F:20])[CH:22]=1)[CH:8]=[CH:7]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 1049Pyridine2×HCID 61668Boronic Acid2×HCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 583038564-(benzyloxy)-7-bromo-5-fluoro-1H-indole

Produkt 1

HCID 596279357-bromo-5-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indoleAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 8895Cupric acetateKatalysator2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 7-bromo-5-fluoro-4-[(phenylmethyl)oxy]-1H-indole (D5) (3 g, 9.37 mmol), {3-fluoro-4-[(phenylmethyl)oxy]phenyl}boronic acid (3.46 g, 14.06 mmol), copper (II) acetate (2.55 g, 14.06 mmol) and pyridine (0.834 mL, 0.815 g, 10.31 mmol) in dichloromethane (50 mL) were stirred together vigorously under an air atmosphere with powdered 4A molecular sieves (˜10 g). After stirring for 20 hours, another 0.5 g of boronic acid were added and the mixture was stirred for a further 24 hours. Then another 1.73 g boronic acid (0.75 eq), copper acetate (1.28 g, 0.75 eq) and pyridine (1.52 mL, 2 eq) were added and stirring was continued at room temperature. After a further 24 hours, the reaction was diluted with ethyl acetate and filtered through celite. The celite was washed with ethyl acetate and the combined filtrates were washed with water (2×), dried (Na2SO4) and concentrated. Chromatography SP4 (0-30% ethyl acetate in hexane) gave the title compound as a white solid (D6), (1.463 g).

Aufarbeitung

  1. stirringthe mixture was stirred for a further 24 hours
  2. stirringstirring
  3. customwas continued at room temperature
  4. waitAfter a further 24 hours
  5. filtrationfiltered through celite
  6. washThe celite was washed with ethyl acetate
  7. washthe combined filtrates were washed with water (2×)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-09c761198be24bf9a6dd5fea6443048a
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07956083B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion