Cesium fluoride → HCID 90118179, Verbindung

HRID 523145

Reaktionsgleichung

Reaktionsgleichung von HRID 523145
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1)CCC.[F-].[Cs+]>[Cu]I.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:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=[C:2]([C:24]2[N:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 901180792,4-Dichloro-6-(4-isopropoxyphenyl)pyridine

Produkt 1

HCID 90118179HCID 90118179, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

To a 2 dram vial equipped with a stir bar was added 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine (50 mg, 0.18 mmol), 2-(tributylstannyl)pyrimidine (65 mg, 0.18 mmol), CuI (8 mg, 0.04 mmol), CsF (81 mg, 0.53 mmol), and Pd(PPh3)4 (10 mg, 8.9 μmol). The vial was capped with a septum screw-cap and then placed under N2 atmosphere. To the vial was added degassed DMF (1 mL). The vial was placed in a 80° C. heating block with stirring for 1 hour. The mixture was allowed to cool to room temperature, and the reaction mixture was then directly subjected to C18 chromatography (water:MeOH w/0.1% TFA) to afford 2-(4-chloro-6-(4-isopropoxyphenyl)pyridin-2-yl)pyrimidine as an amber solid. This material was carried forward into step 2.

Aufarbeitung

  1. customTo a 2 dram vial equipped with a stir bar
  2. customThe vial was capped with a septum
  3. customscrew-cap
  4. additionTo the vial was added
  5. customdegassed DMF (1 mL)
  6. customwas placed in a 80° C.
  7. temperatureheating block

Quellen und Nachweise

ORD-Eintrag
ord-a20a0a571a7445be80c3fdf900ddb2c7
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334279B2

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