Sodium Carbonate → 4-(3-Trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)-[2,4']bipyridinyl

HRID 347699

Reaktionsgleichung

Reaktionsgleichung von HRID 347699
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[N:7][N:6]2[C:9]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:25]=[CH:24]C=C[C:19]=4[C:20]#[N:21])[CH:13]=3)=[CH:10][N:11]=[C:5]2[N:4]=1.N1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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:1][C:2]([F:26])([F:27])[C:3]1[CH:8]=[N:7][N:6]2[C:9]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:25]=[CH:24][N:21]=[CH:20][CH:19]=4)[CH:13]=3)=[CH:10][N:11]=[C:5]2[N:4]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 99071722-[4-(3-Trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)pyridin-2-yl]-benzonitrile

Produkt 1

HCID 100429834-(3-Trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)-[2,4']bipyridinylAusbeute 24,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 7-(2-chloropyridin-4-yl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.10 g, 0.33 mmol) (prepared as described in Example 1), pyridine-4-boronic acid (50 mg, 0.40 mmol) and sodium carbonate (600 μl of a 2 M solution) in 1,4-dioxane (3 ml) was degassed by bubbling nitrogen through for 20 min. Tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.04 mmol) was added and the mixture heated at 90° C. for 4 h. Solvent was removed in vacuo from the mixture and the residue partitioned between dichloromethane (50 ml) and water (30 ml). The organic layer was washed with saturated brine then dried (MgSO4), filtered and evaporated in vacuo. Purification by chromatography (silica gel, 5% MeOH/CH2Cl2) gave 28 mg of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.98–7.99 (2H, m), 8.06 (1H, dd, J 1.6, 5.1), 8.59 (1H, s), 8.79–8.84 (3H, m), 8.94 (1H, dd, J 0.8, 4.3), 8.95 (1H, s); MS (ES+) m/z 343 [M+H]+.

Aufarbeitung

  1. customwas degassed
  2. customby bubbling nitrogen through for 20 min
  3. customSolvent was removed in vacuo from the mixture
  4. customthe residue partitioned between dichloromethane (50 ml) and water (30 ml)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customPurification by chromatography (silica gel, 5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-adcf6c22613d4ec89aa12868dce46666
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176203B2

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