Dimethylformamide → HCID 86761038, Verbindung

HRID 1990839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1990839
Br[C:2]1[CH:3]=[C:4](OCC)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.BrC1N=C(OC)[C:17]([O:22]CC)=[CH:16]C=1.[Li]CCCC.CN([CH:33]=[O:34])C.[Cl-].[NH4+]>C1COCC1>[CH2:17]([O:22][C:7]1[C:2]([CH:33]=[O:34])=[CH:3][CH:4]=[C:5]([O:8][CH3:9])[N:6]=1)[CH3:16]

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 666174095-Bromo-3-ethoxy-2-methoxypyridineHCID 86607632Pyridine, 6-bromo-3-ethoxy-2-methoxy-HCID 178418339Butyllithium

Produkt 1

HCID 86761038HCID 86761038, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 3:2 mixture of 5-bromo-3-ethoxy-2-methoxy-pyridine and 6-bromo-3-ethoxy-2-methoxy-pyridine (1.0 g, 4.31 mmol, 1.0 equiv) in anhydrous THF (20 mL) was added at −78° C. under Ar a solution of n-BuLi (3.23 mL, 5.17 mmol, 1.2 equiv, 1.6 M solution in hexane). After stirring for 1 h, anhydrous DMF (0.7 mL, 9.05 mmol, 2.1 equiv) was added and the reaction mixture stirred for an additional 30 min. A sat. solution of ammonium chloride (20 mL) was added and the solution extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified by twice recrystallization from isopropanol yielding 0.35 g (75%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.50 (t, J=7.0 Hz, 3H), 4.11 (s, 3H), 4.15 (q, J=7.0 Hz, 2H), 7.46 (d, J=1.9 Hz, 1H), 8.19 (d, J=1.9 Hz, 1H), 9.93 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.44, 54.67, 64.59, 113.72, 127.59, 144.29, 144.31, 158.80, 189.66. MS (ISP): 181.8 [M+H]+.

Aufarbeitung

  1. stirringthe reaction mixture stirred for an additional 30 min
  2. extractionthe solution extracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvent removed by evaporation under reduced pressure
  5. customthe crude material purified by twice recrystallization from isopropanol yielding 0.35 g (75%) of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-d98b01d0614c4c4cba5b68e0fb26833c
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645753B2

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