Sodium Nitrite → 5-cyclopropyl-1H-pyrazolo[3,4-c]pyridine

HRID 1527300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527300
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH3:11])[CH:5]=2)[CH2:3][CH2:2]1.[N:12]([O-])=O.[Na+]>CC(O)=O.O>[CH:1]1([C:4]2[CH:5]=[C:6]3[CH:11]=[N:12][NH:10][C:7]3=[CH:8][N:9]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 23668193Sodium NitriteHCID 682833106-Cyclopropyl-4-methylpyridin-3-amine

Produkt 1

HCID 682844125-cyclopropyl-1H-pyrazolo[3,4-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 6-cyclopropyl-4-methylpyridin-3-amine (130 mg, 0.88 mmol) in AcOH (10 mL) was treated with a solution of sodium nitrite (61 mg, 0.88 mmol) in water (0.5 mL). The reaction mixture was stirred at RT for 15 min and then was allowed to stand at RT for 24 h. AcOH was evaporated under reduced pressure and the residual aqueous solution was partitioned between EtOAc and sat. aq. NaHCO3. The organic solution was washed with water and brine, then dried (Phase separator) and concentrated under. MS (LC-MS): 160 [M+H]+, tR (HPLC conditions c): 2.07 min.

Aufarbeitung

  1. waitto stand at RT for 24 h
  2. customAcOH was evaporated under reduced pressure
  3. customthe residual aqueous solution was partitioned between EtOAc and sat. aq. NaHCO3
  4. washThe organic solution was washed with water and brine
  5. customdried (Phase separator)
  6. concentrationconcentrated under
  7. custom2.07 min.

Quellen und Nachweise

ORD-Eintrag
ord-e9adfbd507fd4e1bba64e046ae86d72b
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

Notizen zur Reaktion

Wird geladen…