Potassium Carbonate → HCID 57761071, Verbindung

HRID 230936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230936
Cl[C:2]1[C:7]([CH3:8])=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[N:5]=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:3]=1.[Cl:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:37]=1[F:38].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[Cl:31][C:32]1[CH:33]=[C:34]([C:2]2[C:7]([CH3:8])=[C:6]([N:9]3[CH2:14][CH2:13][N:12]([C:15]4[C:20]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:18]=[CH:17][N:16]=4)[CH2:11][CH2:10]3)[N:5]=[C:4]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:3]=2)[CH:35]=[CH:36][C:37]=1[F:38]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 57761798HCID 57761798, Verbindung

Produkt 1

HCID 57761071HCID 57761071, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-(4-chloro-5-methyl-6-{4-[3-(trifluoromethyl)(2-pyridyl)]piperazinyl}pyrimidin-2-yl)morpholine (66 mg, 0.15 mmol), 3-chloro-4-fluorophenylboronic acid (35 mg, 0.2 mmol), Pd(PPh3)4 (10 mg) and 2M potassium carbonate (0.2 mL) in toluene (3 mL) is heated, under a nitrogen atmosphere, at 80° C. for 4 hours. The reaction mixture is cooled and the layers separated. The aqueous layer is extracted with EtOAc (3×10 mL) and the combined organics washed with 4M NaOH (10 mL), water (10 mL), brine (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (70% hexane/30% ether) to give the title compound. MS 537 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. customthe layers separated
  3. extractionThe aqueous layer is extracted with EtOAc (3×10 mL)
  4. washthe combined organics washed with 4M NaOH (10 mL), water (10 mL), brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography on silica gel (70% hexane/30% ether)

Quellen und Nachweise

ORD-Eintrag
ord-7f80605c1e7549eaa48d67495ca2057b
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566712B2

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