Stannane → 3-(Furan-2-yl)-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2,4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine

HRID 276763

Reaktionsgleichung

Reaktionsgleichung von HRID 276763
Br[C:2]1[C:3]([O:17][CH2:18][C:19]2[N:23]([CH3:24])[N:22]=[CH:21][N:20]=2)=[N:4][N:5]2[C:10]=1[CH:9]=[N:8][N:7]=[C:6]2[C:11]1[CH:15]=[C:14]([CH3:16])[O:13][N:12]=1.C([Sn](CCCC)(CCCC)[C:30]1[O:31][CH:32]=[CH:33][CH:34]=1)CCC.[SnH4]>O1CCOCC1.[Pd]>[O:31]1[CH:32]=[CH:33][CH:34]=[C:30]1[C:2]1[C:3]([O:17][CH2:18][C:19]2[N:23]([CH3:24])[N:22]=[CH:21][N:20]=2)=[N:4][N:5]2[C:10]=1[CH:9]=[N:8][N:7]=[C:6]2[C:11]1[CH:15]=[C:14]([CH3:16])[O:13][N:12]=1

Komponenten

6

Edukt 3

HCID 123161StannaneHCID 43936882-(Tributylstannyl)furanHCID 226291463-Bromo-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2, 4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine

Produkt 1

HCID 226291403-(Furan-2-yl)-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2,4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazineAusbeute 196,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A stirred mixture of 3-bromo-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2,4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine (Example 7) (80 mg, 0.20 mmol) in dioxan (10 mL) containing 2-tri-n-butylstannylfuran (146 mg, 0.41 mmol) was degassed with nitrogen for 20 min. Tetrakis-triphenylphosphine palladium(0) (50 mg) and copper(I)iodide (5 mg) were added and the mixture heated at reflux for 8 h. Further stannane (146 mg, 0.41 mmol) and palladium catalyst (50 mg) were added and the mixture heated at reflux for 16 h. The solvent was evaporated and the residue purified on silica eluting with 5% MeOH/DCM to give a yellow solid (149 mg). The yellow solid was re-chromatographed on silica eluting with 5% MeOH/DCM to give a yellow solid (29 mg) which was triturated with diethylether to give the title compound (15 mg, 19%) as a yellow solid. mp 226-228° C. 1H NMR (360 MHz, CDCl3) δ1.58 (9H, s), 2.61 (3H, s), 4.10 (3H, s), 5.78 (2H, s), 6.52-6.56 (1H, m), 6.75-6.79 (1H, m), 6.96 (1H, s), 7.57 (1H, s), 7.91 (1H, s), 9.71 (1H, s). Found: C, 52.68; h, 3.47; N, 28.64; C17H14N8O3.0.05(CH2Cl2).0.25(H2O) requires: C, 52.90; H, 28.95%.

Aufarbeitung

  1. customwas degassed with nitrogen for 20 min
  2. additionTetrakis-triphenylphosphine palladium(0) (50 mg) and copper(I)iodide (5 mg) were added
  3. temperaturethe mixture heated
  4. temperatureat reflux for 8 h
  5. temperaturethe mixture heated
  6. temperatureat reflux for 16 h
  7. customThe solvent was evaporated
  8. customthe residue purified on silica eluting with 5% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-a07aef879027416f8f6d1cfa8487eda3
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355638B1

Verknüpfte Notizen

Wird geladen…