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Pyridine → 1-{3,5-Difluoro-4-[(phenyl methyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole

HRID 2423089
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2423089
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([F:33])[C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:18][C:19]1[CH:20]=[C:21]([N:13]2[C:14]3[C:10](=[C:9]([O:8][CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:17]=[CH:16][CH:15]=3)[CH:11]=[N:12]2)[CH:22]=[C:23]([F:33])[C:24]=1[O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 231344734-(Benzyloxy)-1h-indazoleHCID 54758874(4-(Benzyloxy)-3,5-difluorophenyl)boronic acid

Produkt 1

HCID 592729551-{3,5-Difluoro-4-[(phenyl methyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 4-[(phenylmethyl)oxy]-1H-indazole (D1) (280 mg, 1.25 mmol) in dichloromethane (20 mL) was added {3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}boronic acid {DE patent application 4236105} (660 mg, 2.50 mmol), pyridine (0.202 mL, 2.50 mmol), copper acetate (340 mg, 1.88 mmol) and powdered 4A molecular sieves (500 mg). The reaction mixture was stirred at room temperature in the presence of air for 6 days. Celite was added to the mixture then the mixture was filtered through a pad of celite and then the filtrate was washed with water. After separation of the layers, the aqueous phase was re-extracted with dichloromethane. The combined organic layers were dried over magnesium sulphate, filtered and concentrated. The product was purified by silica gel chromatography eluting with 5-100% ethyl acetate in hexane to yield the title compound (D35 (257 mg).

Aufarbeitung

  1. additionCelite was added to the mixture
  2. filtrationthe mixture was filtered through a pad of celite
  3. washthe filtrate was washed with water
  4. customAfter separation of the layers
  5. extractionthe aqueous phase was re-extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by silica gel chromatography
  10. washeluting with 5-100% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-f63ead05786c4eb89b6ac17b49fe0f2f
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07960563B2

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