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Diethyl Ether → Methyl 3-azido-6-bromo-6'-morpholino-2,3'-bipyridine-4-carboxylate

HRID 2410752
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2410752
[NH2:1][C:2]1[C:3]([C:13]2[CH:14]=[N:15][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:17][CH:18]=2)=[N:4][C:5]([Br:12])=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].N([O-])=O.[Na+].[N-:29]=[N+:30]=[N-].[Na+].CCOCC>C(O)(C(F)(F)F)=O.O>[N:1]([C:2]1[C:3]([C:13]2[CH:14]=[N:15][C:16]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:17][CH:18]=2)=[N:4][C:5]([Br:12])=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[N+:29]=[N-:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 86663022Methyl 3-amino-6-bromo-6'-morpholino-2,3'-bipyridine-4-carboxylate

Produkt 1

HCID 86663023Methyl 3-azido-6-bromo-6'-morpholino-2,3'-bipyridine-4-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Methyl 3-amino-6-bromo-6′-morpholino-2,3′-bipyridine-4-carboxylate (230 mg, 0.59 mmol) was dissolved in TFA (2.9 mL) and the solution was cooled in an ice bath. Solid sodium nitrite (89 mg, 1.29 mmol) was added slowly with stirring to give a red solution. After 30 min, powdered sodium azide (380 mg, 5.85 mmol) was added in portions with gas evolution. Et2O (29 mL) was added with stirring after 0.5 hr, water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with, water (3×), saturated Na2CO3 solution (until the aqueous phase was basic), and brine (1×). After drying the solvent with sodium sulfate, the solvent was removed. Flash chromatography (step gradient elution with DCM containing 0 to 20% EtOAc) afforded methyl 3-azido-6-bromo-6′-morpholino-2,3′-bipyridine-4-carboxylate (240 mg, 0.57 mmol, 98% yield) yellow solid. 1H NMR (500 MHz, chloroform-d) δ ppm 8.73 (1H, d, J=2.44 Hz), 7.99 (1H, dd, J=9.00, 2.59 Hz), 7.71 (1H, s), 6.68 (1H, d, J=8.85 Hz), 4.00 (3H, s), 3.79-3.86 (4H, m), 3.59-3.66 (4H, m).

Aufarbeitung

  1. temperaturethe solution was cooled in an ice bath
  2. customto give a red solution
  3. stirringwith stirring after 0.5 hr
  4. extractionthe mixture was extracted with EtOAc
  5. washThe combined organic extracts were washed with, water (3×), saturated Na2CO3 solution (until the aqueous phase
  6. dry with materialAfter drying the solvent with sodium sulfate
  7. customthe solvent was removed
  8. washFlash chromatography (step gradient elution with DCM containing 0 to 20% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-66317d6883524e70b31e53e571173fac
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08815840B2

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