Nitrogen → 2-(2-Methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-pyrazol-1-ylmethyl)-pyridine

HRID 2064967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064967
N#N.[CH3:3][C:4]1([C:9]2[N:14]=[C:13]([CH2:15]OS(C)(=O)=O)[CH:12]=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[N+:21]([C:24]1[CH:25]=[N:26][NH:27][CH:28]=1)([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+].[I-]>CC(C)=O>[CH3:3][C:4]1([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH2:15][N:26]3[CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]3)[N:14]=2)[O:5][CH2:6][CH2:7][O:8]1

Komponenten

7

Edukt 5

HCID 947Nitrogen2×HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 30165Iodide IonHCID 86649482Methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester

Produkt 1

HCID 669289362-(2-Methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-pyrazol-1-ylmethyl)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester (273 mg, 1.00 mmol) in acetone (4.0 mL) was added, under inert atmosphere (N2) to a solution of 4-nitro-1H-pyrazole (115 mg, 1.00 mmol) in acetone (4.0 mL). K2CO3 (698 mg, 5.00 mmol) and TBA iodide (64 mg, 0.20 mmol) were added and the reaction mixture was stirred at rt for 5 h. The solvent was removed under reduced pressure. Water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (30:10 to 50:50 hept-EA) gave the title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.87 min; [M+H]+=291.27.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionWater (10 mL) and EA (10 mL) were added
  3. extractionThe aq. layer was extracted with EA (10 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (30:10 to 50:50 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-c16fb77f6c534b768e0753b8fdedaa8e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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