Pyridine → [5-(1-Methyl-cyclopropyl)-2-(6-methyl-pyridin-3-yl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 1993676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993676
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].F[C:11](F)(F)[C:12]1([C:15]2[CH:16]=[C:17]([NH2:27])[N:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=C[CH:21]=3)[N:19]=2)[CH2:14][CH2:13]1.[N:30]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.ClCCl>[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](=[O:6])[NH:27][C:17]1[N:18]([C:20]2[CH:21]=[N:30][C:23]([CH3:26])=[CH:24][CH:25]=2)[N:19]=[C:15]([C:12]2([CH3:11])[CH2:13][CH2:14]2)[CH:16]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 668765651-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

Produkt 1

HCID 68538118[5-(1-Methyl-cyclopropyl)-2-(6-methyl-pyridin-3-yl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl esterAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Add a solution of 2,2,2-trichloroethylchloroformate (1.80 g, 8.5 mmol) in THF (10 mL) dropwise to an ice-salt cooled solution of 5-(1-trifluoromethyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine (2.29 g, 8.1 mmol) and pyridine (0.9 mL, 11 mmol) in THF (30 mL) at −15° C. Stir at −15° C. for 0.5 hours and then 22° C. for 1 hour, then distribute the reaction mixture between dichloromethane (50 mL) and a saturated aq. sodium bicarbonate solution (50 mL). Isolate the aqueous phase and extract twice with dichloromethane (25 mL each). Dry the combined organic phases over sodium sulfate and concentrate. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to give a white solid (2.46 g, 66% yield). MS(ES+): m/z=457.2 [M+H].

Aufarbeitung

  1. wait22° C. for 1 hour
  2. customIsolate the aqueous phase
  3. extractionextract twice with dichloromethane (25 mL each)
  4. dry with materialDry the combined organic phases over sodium sulfate
  5. concentrationconcentrate
  6. washSubject residue to silica gel chromatography eluting with hexanes and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-984b9d82af544506a7f3a2f375157f9f
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652015B2

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