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Cesium carbonate → 7-(2-Fluorophenyl)-4-methyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-3-(thien-3-yl)pyrazolo[1,5-d][1,2,4]triazine

HRID 985443
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 985443
Br[C:2]1[C:3]([O:19][CH2:20][C:21]2[N:22]([CH3:26])[N:23]=[CH:24][N:25]=2)=[N:4][N:5]2[C:10]=1[C:9]([CH3:11])=[N:8][N:7]=[C:6]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18].[S:27]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:6]1[N:5]2[N:4]=[C:3]([O:19][CH2:20][C:21]3[N:22]([CH3:26])[N:23]=[CH:24][N:25]=3)[C:2]([C:29]3[CH:30]=[CH:31][S:27][CH:28]=3)=[C:10]2[C:9]([CH3:11])=[N:8][N:7]=1
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Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 581760Thiophene-3-boronic acidHCID 225068923-bromo-7-(2-fluorophenyl)-4-methyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine

Produkt 1

HCID 101804997-(2-Fluorophenyl)-4-methyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-3-(thien-3-yl)pyrazolo[1,5-d][1,2,4]triazine
Ausbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 3-bromo-7-(2-fluorophenyl)-4-methyl-2-(2-methyl-2H-[1,2,4]triazol-3ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine (100.7 mg, 0.241 mmol), thiophene-3-boronic acid (46.8 mg, 0.366 mmol) and cesium carbonate (157.0 mg, 0.482 mmol) in anhydrous 1,4-dioxane (10 ml) was degassed by three freeze-pump-thaw cycles. Then tris(dibenzylideneacetone)dipalladium(0) (22.5 mg, 0.0246 mmol) and a 0.1M solution of tri-tert-butylphosphine in 1,4-dioxane (0.58 ml, 0.058 mmol) was added and two more freeze-pump-thaw cycles were performed. The mixture was heated at 90° C. under nitrogen for 22 h, then filtered through glass fibre paper. The solid was washed with ethyl acetate, and the filtrates were washed with saturated aqueous NaCl (15 ml). The aqueous layer was further extracted with ethyl acetate (25 ml), and the combined extracts were dried (NaSO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 2% MeOH/CH2Cl2) to give 83.8 mg (83%) of the title compound as an orange solid: mp=124-129° C. (CH2Cl2-EtOAc-isohexane); 1H NMR (360 MHz, CDCl3) δ 2.60 (3H, s), 3.71 (5H, s), 5.46 (2H, s), 7.18 (1H, d, J=4.9 Hz), 7.27 (1H, m), 7.38 (1H, m), 7.38 (1H, s), 7.44 (1H, dd, J=4.9, 3.0 Hz), 7.63 (1H, m), 7.75 (1H, t, J=7.1 Hz), 7.83 (1H, s); MS (ES+) m/e 422 [M+H]+. Anal. Found C, 56.94; H, 4.04; N, 22.49%. C20H16FN7OS.0.08 C4H8O2 requires C, 56.96; H, 3.91; N, 22.88%.

Aufarbeitung

  1. customwas degassed by three freeze-pump-thaw cycles
  2. filtrationfiltered through glass fibre paper
  3. washThe solid was washed with ethyl acetate
  4. washthe filtrates were washed with saturated aqueous NaCl (15 ml)
  5. extractionThe aqueous layer was further extracted with ethyl acetate (25 ml)
  6. dry with materialthe combined extracts were dried (NaSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (silica gel, 2% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-fa58322fdd624fafa3c9c5f72eef63d3
Quelldatensatz
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06872720B2

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