Sodium Carbonate → HCID 89649230, Verbindung

HRID 2207598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207598
Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH2:13][CH2:12][C:11]3([CH2:17][CH2:16][N:15]([CH3:18])[C:14]3=[O:19])[N:10]=2)[CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:29]=2[C:30]#[N:31])O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][C:6]1[CH:7]=[C:2]([C:28]2[CH:35]=[C:34]([C:36]([F:37])([F:39])[F:38])[CH:33]=[CH:32][C:29]=2[C:30]#[N:31])[CH:3]=[C:4]([C:9]2[CH2:13][CH2:12][C:11]3([CH2:17][CH2:16][N:15]([CH3:18])[C:14]3=[O:19])[N:10]=2)[N:5]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 569731072-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzonitrileHCID 89649623HCID 89649623, Verbindung

Produkt 1

HCID 89649230HCID 89649230, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178419050HCID 178419050, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 2-(4-bromo-6-methyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 13) (180 mg, 0.5600 mmol) in 1,2-dimethoxyethane (3 mL) and water (1 mL) was added 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzonitrile (182.56 mg, 0.6100 mmol) and sodium carbonate (177.65 mg, 1.68 mmol). The reaction mixture was degassed with nitrogen and then treated with bis(triphenylphosphine)palladium (II) dichloride (19.61 mg, 0.0300 mmol). The reaction was heated in the microwave at 120° C. for 15 minutes. The reaction mixture was diluted with dichloromethane and water. After separation of the layers, the aqueous phase was re-extracted with dichloromethane and the combined organic phases passed through a hydrophobic frit. The solvent was evaporated and the residue purified by silica gel chromatography to afford 2-[2-methyl-6-(7-methyl-6-oxo-1,7-diazaspiro[4.4]non-1-en-2-yl)-4-pyridyl]-4-(trifluoromethyl)-benzonitrile (D14) as a colourless solid (74 mg);

Aufarbeitung

  1. customThe reaction mixture was degassed with nitrogen
  2. customAfter separation of the layers
  3. extractionthe aqueous phase was re-extracted with dichloromethane
  4. customThe solvent was evaporated
  5. customthe residue purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-21a079ecbe5947ef85f20fe1af4496ee
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376436B2

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