Sodium Nitrite → 5-(Trifluoromethyl)-1H-pyrazolo[3,4-C]pyridine

HRID 1527304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527304
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][C:3]=1[NH2:12].[N:13]([O-])=O.[Na+]>C(O)(=O)C.O>[F:10][C:8]([F:11])([F:9])[C:6]1[CH:7]=[C:2]2[CH:1]=[N:13][NH:12][C:3]2=[CH:4][N:5]=1

Komponenten

5

Edukt 2

HCID 23668193Sodium NitriteHCID 497579514-Methyl-6-(trifluoromethyl)pyridin-3-amine

Produkt 1

HCID 682833945-(Trifluoromethyl)-1H-pyrazolo[3,4-C]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-methyl-6-(trifluoromethyl)pyridin-3-amine [944317-54-8] (1.00 g, 5.68 mmol) in acetic acid (75 mL) was treated with a solution of sodium nitrite (392 mg, 5.68 mmol) in water (1 mL). The reaction mixture was stirred at RT for 15 min and then was allowed to stand at ambient temperature for 48 h. Acetic acid 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 vacuum. MS (LC-MS): 188 [M+H]+, tR (HPLC conditions k): 2.49 min.

Aufarbeitung

  1. waitto stand at ambient temperature for 48 h
  2. customAcetic acid 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 vacuum
  7. custom2.49 min.

Quellen und Nachweise

ORD-Eintrag
ord-3523a765bb9d4d61ad5ae53a73f00d9f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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