Potassium Carbonate → 3-(4-Amino-2-fluorophenyl)-5-bromopyridin-2-amine

HRID 1428097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428097
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1B1OC(C)(C)C(C)(C)O1)[NH2:14].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>O1CCOCC1.O.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>[NH2:14][C:13]1[CH:15]=[CH:16][C:17]([C:4]2[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[C:11]([F:10])[CH:12]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 15165082-Amino-5-bromo-3-iodopyridineHCID 447552073-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Produkt 1

HCID 867000473-(4-Amino-2-fluorophenyl)-5-bromopyridin-2-amineAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-Bromo-3-iodopyridin-2-amine (300 mg), 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (238 mg), tetrakis(triphenylphosphine)palladium (58 mg) and potassium carbonate (416 mg) were suspended in dioxane (5 ml) and water (0.5 ml), and the suspension was heated under reflux at 80° C. for two days. After leaving to cool, a saturated aqueous sodium bicarbonate solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [hexane:ethyl acetate=1:2 (v/v)] to give 248 mg of the title compound as a solid.

Aufarbeitung

  1. customAfter leaving
  2. temperatureto cool
  3. extractionthe organic layer was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [hexane:ethyl acetate=1:2 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-9e855f16dac34369b4d194728a9c6b29
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933103B2

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