Tetramethyltin → 5-Methyl-6-(2-methyl-2h-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1h-pyrazolo[3,4-b]pyridine

HRID 1263491

Reaktionsgleichung

Reaktionsgleichung von HRID 1263491
Br[C:2]1[CH:3]=[C:4]2[CH:18]=[N:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]2=[N:6][C:7]=1[O:8][CH2:9][C:10]1[N:11]([CH3:15])[N:12]=[CH:13][N:14]=1.[CH3:25][Sn](C)(C)C>CN(C)C(=O)C.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.Cl[Pd]Cl>[CH3:25][C:2]1[CH:3]=[C:4]2[CH:18]=[N:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]2=[N:6][C:7]=1[O:8][CH2:9][C:10]1[N:11]([CH3:15])[N:12]=[CH:13][N:14]=1

Komponenten

5

Edukt 2

HCID 11661TetramethyltinHCID 186168255-bromo-6-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1H-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 102679885-Methyl-6-(2-methyl-2h-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1h-pyrazolo[3,4-b]pyridineAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10876480Bis(tri-o-tolylphosphine)palladium(II) DichlorideKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a de-gassed solution of 5-bromo-6-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1H-pyrazolo[3,4-b]pyridine (84 mg, 0.22 mmol) in N,N-dimethylacetamide (2 ml) was added tetramethyltin (60 μl, 0.43 mmol) followed by dichlorobis(tri-ortho-tolylphosphine)palladium(II) (8.6 mg, 0.01 mmol). The reaction mixture was heated at 90° C. in a sealed tube for 20 h. The mixture was allowed to cool, quenched with saturated aqueous ammonium chloride solution and the product extracted into diethyl ether (×3). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by preparative thin layer chromatography, eluting with 55% ethyl acetate-hexane, afforded the title compound as a white solid (20 mg, 29%), m.p. 145-146° C. δH (400 MHz; CDCl3) 2.32 (3H, s), 3.96 (3H, s), 5.66 (2H, s), 7.31 (1H, t, J=7), 7.50-7.54 (2H, m), 7.82 (1H, s), 7.91 (1H, s), 8.02 (1H, s), 8.19-8.22 (2H, m); m/z (ES+) 321 (M+H+).

Aufarbeitung

  1. temperatureto cool
  2. customquenched with saturated aqueous ammonium chloride solution
  3. extractionthe product extracted into diethyl ether (×3)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by preparative thin layer chromatography
  8. washeluting with 55% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-14d1c67b7b7a45c298c91c37d8857ba6
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541484B2

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