Potassium Phosphate, Tribasic → (3-Fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine

HRID 711225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711225
[CH3:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.Cl[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][C:13]=1[F:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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>[F:20][C:13]1[CH:14]=[C:15]([CH2:18][NH2:19])[CH:16]=[CH:17][C:12]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2757541(4-Chloro-3-fluorophenyl)methanamineHCID 41926642-Methylpyridine-4-boronic acid

Produkt 1

HCID 67208674(3-Fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
96 °C

Versuchsvorschrift

A mixture of (2-methylpyridin-4-yl)boronic acid 15-1 (822 mg, 6.2 mmol), (4-chloro-3-fluorophenyl)methanamine 15-2 (798 mg, 5.00 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol) and K3PO4 (1.59 g, 7.50 mmol) in dioxane (10 mL) and water (1 mL) was stirred at 96° C. under argon overnight. After cooling to room temperature, the mixture was filtered through celite, washed with ethyl acetate, and dried with Na2SO4. The filtrate was concentrated by rotavap and the residue subjected to silica gel column chromatography with 6% ammonia-saturated methanol in dichloromethane as eluent to give (3-fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine 15-3 as an oil.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. dry with materialdried with Na2SO4
  5. concentrationThe filtrate was concentrated by rotavap

Quellen und Nachweise

ORD-Eintrag
ord-002187d7f03e4e508b10ceadff063090
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181235B2

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