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Potassium Phosphate, Tribasic → 3-(2-fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

HRID 1020945
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1020945
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[F:33][C:34]1[CH:39]=[C:38](B(O)O)[CH:37]=[CH:36][N:35]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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]>[F:33][C:34]1[CH:39]=[C:38]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[N:4]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)[CH:37]=[CH:36][N:35]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27833962-Fluoropyridine-4-boronic acidHCID 589464433-bromo-5-nitro-1-trityl-1H-indazole

Produkt 1

HCID 583719213-(2-fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Bromo-5-nitro-1-trityl-1H-indazole 3BI (15.64 g, 32.3 mmol), 2-fluoro-4-pyridine boronic acid 2BV (5.0 g, 35.5 mmol), K3PO4 (17.1 g, 80.7 mmol) and Pd(dppf)Cl2 (2.64 g, 3.23 mmol) was mixed in dioxane/H2O (240 mL/60 mL) at rt and heated at 80° C. overnight. The reaction mixture was cooled to rt and concentrated to a small volume. The residue was partitioned between ethyl acetate (200 mL) and brine (150 mL). The organic layer was washed with brine, dried (MgSO4) and filtered. The resulting filtrate was concentrated and the residue was purified on silica gel column eluting with hexanes, 5% ethyl acetate in hexanes, 10% ethyl acetate in hexanes sequentially to yield a yellow solid 3BV (3.33 g, 64%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated to a small volume
  3. customThe residue was partitioned between ethyl acetate (200 mL) and brine (150 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe resulting filtrate was concentrated
  8. customthe residue was purified on silica gel column
  9. washeluting with hexanes, 5% ethyl acetate in hexanes, 10% ethyl acetate in hexanes sequentially
  10. customto yield a yellow solid 3BV (3.33 g, 64%)

Quellen und Nachweise

ORD-Eintrag
ord-542fcdd65bef4bacbc658574ac44e3ac
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08716483B2

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