Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate → Methyl thieno(3,2-b)pyridine-2-carboxylate

HRID 335550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335550
N[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].N([O-])=O.[Na+]>>[S:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[CH:2]=[C:3]1[C:11]([O:13][CH3:14])=[O:12]

Komponenten

3

Edukt 2

HCID 13793447Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylateHCID 23668193Sodium Nitrite

Produkt 1

HCID 22047416Methyl thieno(3,2-b)pyridine-2-carboxylate

Versuchsvorschrift

The synthesis is carried out according to the general procedure; for work-up, the resulting precipitate is filtered off with suction and washed repeatedly with water, ethyl acetate and THF. The organic phases of the resulting filtrates are separated off, the aqueous phase is washed with ethyl acetate and the combined organic phases are dried and concentrated. The resulting product is purified by preparative HPLC. Using 2.40 g (11.53 mmol) of methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate and 2.54 g (36.88 mmol) of sodium nitrite, 0.12 g (5% of theory) of the desired product are obtained.

Aufarbeitung

  1. filtrationfor work-up, the resulting precipitate is filtered off with suction
  2. washwashed repeatedly with water, ethyl acetate and THF
  3. customThe organic phases of the resulting filtrates are separated off
  4. washthe aqueous phase is washed with ethyl acetate
  5. customthe combined organic phases are dried
  6. concentrationconcentrated
  7. customThe resulting product is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2948b30df94f465091043cbcfc357926
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884017B2

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