Potassium Phosphate, Tribasic → 5-Amino-1-(4-fluorophenyl)-4-[3-(pyridin-3-yl)benzoyl]pyrazole

HRID 429356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429356
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1.B1(C2C=CC=NC=2)OCCCO1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cl-].[Na+].O>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)[CH:16]=1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 114512375-Amino4-(3-bromobenzoyl)-1-(4-fluorophenyl)pyrazole

Produkt 1

HCID 99506645-Amino-1-(4-fluorophenyl)-4-[3-(pyridin-3-yl)benzoyl]pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 5-amino-4-(3-bromobenzoyl)-1-(4-fluorophenyl)pyrazole (0.9 g, 2.5 mmol) [prepared as described in Example 1 above], pyridine-3-boronic acid, 1,3-propanediol cyclic ester (0.5 g, 3 mmol), potassium phosphate (0.8 g, 3.73 mmol) and tetrakistriphosphine palladium (0.3 g, 0.25 mmol) in dioxane (20 ml) was heated at 85° C. under argon. After 16 h, the reaction mixture was cooled to room temperature and poured into brine. The product was extracted into ethyl acetate, dried over sodium sulfate and filtered. The organic layer was removed in vacuo and the residue was purified by flash chromatography (elution gradient: 40-80% ethyl acetate/hexane) to give 5-amino-1-(4-fluorophenyl)-4-[3-(pyridin-3-yl)benzoyl]-pyrazole (0.50 g) which was recrystallized from ethyl acetate (mpt. 222.2-223.0).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted into ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe organic layer was removed in vacuo
  6. customthe residue was purified by flash chromatography (elution gradient: 40-80% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d3c079038e7447bfa88d35db32334139
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316466B1

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