Triethylamine → 5-Methoxy-3-methyl-1H-pyrrolo[3,2-b]pyridine

HRID 2382144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382144
[CH2:1]([N:4]([C:11]1[C:12](Br)=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)C(=O)C(F)(F)F)[CH:2]=[CH2:3].[Cl-].C([NH3+])CCC.C([NH3+])CCC.C([NH3+])CCC.C([NH3+])CCC.[Cl-].[Cl-].[Cl-].C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][C:14]1[N:13]=[C:12]2[C:2]([CH3:3])=[CH:1][NH:4][C:11]2=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 748912193-Bromo-3-(N-allyl-N-trifluoroacetyl)amino-6-methoxypyridineHCID 86639386Tetra(n-butylammonium) chloride

Produkt 1

HCID 151795865-Methoxy-3-methyl-1H-pyrrolo[3,2-b]pyridineAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-allyl-N-(2-bromo-6-methoxy-pyridin-3-yl)-2,2,2-trifluoro-acetamide (5.54 g, 16.3 mmol), palladium acetate (147 mg, 0.65 mmol), tetra(n-butylammonium) chloride (4.99 g, 17.9 mmol) and triethylamine (3.72 g, 26.8 mmol) in anhydrous DMF (35 mL) is stirred at 10° C. under N2 for an hour. DMF is evaporated off, and the residue is mixed with water (20 mL) and stirred at rt overnight. EtOAc (50 mL) is added. The organic layer is separated, dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 30-70% EtOAc in heptane to afford 5-methoxy-3-methyl-1H-pyrrolo[3,2-b]pyridine (2.62 g) as a solid. 1H NMR (300 MHz, CDCl3): δ 2.38 (s, 3H), 4.05 (s, 3H), 6.62 (s, H), 7.12 (s, H), 7.54 (d, H), 7.94 (br, N—H).

Aufarbeitung

  1. customDMF is evaporated off
  2. additionthe residue is mixed with water (20 mL)
  3. additionEtOAc (50 mL) is added
  4. customThe organic layer is separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. washeluting with 30-70% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-64db3a3841334936b8e0cdd681a7944e
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

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