Toluene → 3-(3,5-Difluoropyridin-2-yl)-4-methylaniline

HRID 1890752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890752
Cl[C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=1B1OC(C)(C)C(C)(C)O1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.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.C(O)C>[F:8][C:7]1[C:2]([C:12]2[CH:13]=[C:14]([CH:16]=[CH:17][C:11]=2[CH3:10])[NH2:15])=[N:3][CH:4]=[C:5]([F:9])[CH:6]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 160860894-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 450795602-Chloro-3,5-difluoropyridine

Produkt 1

HCID 583179983-(3,5-Difluoropyridin-2-yl)-4-methylaniline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a round bottom flask is added 2-chloro-3,5-difluoropyridine (1.5 g, 10 mmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.2 g, 10 mmol), Pd(PPh3)4 (300 mg, 0.26 mmol), toluene (60 mL), ethanol (20 mL) and 2M Na2CO3 (20 mL, 40 mmol). The reaction is stirred under reflux condition for 15 hours. After cooling, the reaction mixture is diluted with ethyl acetate, washed with brine and dried over Na2SO4. The organic phase is then dried by rotary evaporation. The crude product is purified by silica gel flash chromatography to afford 3-(3,5-difluoropyridin-2-yl)-4-methylaniline as a light brown solid. MS m/z 221.1 (M+1).

Aufarbeitung

  1. temperatureunder reflux condition for 15 hours
  2. temperatureAfter cooling
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe organic phase is then dried by rotary evaporation
  6. customThe crude product is purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-066678e8fa32466e9350b65845602a5b
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507491B2

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