Water → 2-[Bis(cyclopropylmethyl)amino]-6-fluoropyridine-3-carbaldehyde

HRID 1911795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911795
[CH:1]1([CH2:4][N:5]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:6]2[C:11]([CH2:12]N(CC3C=C(C(F)(F)F)C=C(C(F)(F)F)C=3)C#N)=[CH:10][CH:9]=[C:8]([F:31])[N:7]=2)[CH2:3][CH2:2]1.[OH2:36].[N-]=[N+]=[N-].[Na+]>C(O)(C)C.[Br-].[Zn+2].[Br-]>[CH:1]1([CH2:4][N:5]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:6]2[C:11]([CH:12]=[O:36])=[CH:10][CH:9]=[C:8]([F:31])[N:7]=2)[CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 33557Sodium AzideHCID 58795829HCID 58795829, Verbindung

Produkt 1

HCID 587957962-[Bis(cyclopropylmethyl)amino]-6-fluoropyridine-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10421208Zinc bromideKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To [2-(bis-cyclopropylmethy-amino)-6-fluoro-pyridin-3-ylmethyl]-(3,5-bis-trifluoromethyl-benzyl)-cyanamide (244 mg, 0.5 mmol) stirred in isopropanol (5 mL) and water (10 mL) was added sodium azide (38.4 mg, 0.55 mmol) and zinc bromide (115.6 mg, 0.5 mmol). After stirring at reflux overnight, the solution was extracted with ethyl acetate (2×15 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and then concentrated under vacuum to give the title compound as an orange oily product (248 mg, yield: 91%) and was used as is without purification.

Aufarbeitung

  1. temperatureat reflux overnight
  2. extractionthe solution was extracted with ethyl acetate (2×15 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0cb570ffd2c4425db4cb27f56828182a
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604055B2

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