Methyl iodide → 3,3-dimethyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

HRID 85039

Reaktionsgleichung

Reaktionsgleichung von HRID 85039
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[C:15]3[CH2:21][C:20](=O)[N:19](COCC[Si](C)(C)C)[C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:31](=[O:34])([O-])[O-].[Cs+].[Cs+].[CH3:37]I>CN(C=O)C>[CH3:20][C:21]1([CH3:37])[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:14]=2)[NH:19][C:31]1=[O:34]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 667788935-(3,4,5-Trimethoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one

Produkt 1

HCID 667783683,3-dimethyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-oneAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(3,4,5-trimethoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (43 mg, 0.10 mmol) in DMF (2 mL) was added cesium carbonate (0.17 g, 0.50 mmol) and methyl iodide (19 μL, 0.30 mmol). The resulting solution was stirred for 48 hr at room temperature, after which it was partitioned between EtOAc and H2O. The organic layer was separated, dried over MgSO4, filtered, and concentrated in vacuo. The residue was dissolved in 6 N HCl (10 mL) and MeOH (5 mL), and the resulting mixture was stirred at room temperature overnight, after which it was partitioned between EtOAc and H2O. The organic layer was concentrated in vacuo, and the residue was dissolved in EtOH (2 mL). Potassium acetate (100 mg) was then added, and the reaction was stirred for 2 hr. The resulting solution was purified via preparatory HPLC to give the title compound (24 mg, 73%). 1H NMR (CDCl3, 300 MHz): δ 9.72 (s, 1H), 8.35 (d, J=2.1 Hz, 1H), 7.60 (d, J=1.8 Hz, 1H), 6.71 (s, 2H), 3.95 (s, 6H), 3.90 (s, 3H), 1.49 (s, 6H). HPLC retention time: 1.80 minutes; MS ESI (m/z): 329.4 (M+1)+, calc. 328.

Aufarbeitung

  1. customafter which it was partitioned between EtOAc and H2O
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in 6 N HCl (10 mL)
  7. stirringMeOH (5 mL), and the resulting mixture was stirred at room temperature overnight
  8. customafter which it was partitioned between EtOAc and H2O
  9. concentrationThe organic layer was concentrated in vacuo
  10. dissolutionthe residue was dissolved in EtOH (2 mL)
  11. additionPotassium acetate (100 mg) was then added
  12. stirringthe reaction was stirred for 2 hr
  13. customThe resulting solution was purified via preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a2c7e3b7031e43cf826f944b648940e2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846909B2

Verknüpfte Notizen

Wird geladen…