Water → tert-Butyl 6-(benzyloxy)-3-difluoromethoxyindazole-1-carboxylate

HRID 1873964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873964
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13](=[O:25])[NH:14][N:15]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:33]([F:38])([F:37])C(O)=O.[Na].O>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([O:25][CH:33]([F:38])[F:37])=[N:14][N:15]2[C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 450519421895-39-2HCID 59370717Tert-butyl 6-(benzyloxy)-3-oxo-2,3-dihydroindazole-1-carboxylate

Produkt 1

HCID 45280135tert-Butyl 6-(benzyloxy)-3-difluoromethoxyindazole-1-carboxylateAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Tert-butyl 6-(benzyloxy)-3-oxo-2,3-dihydroindazole-1-carboxylate (342 mg) which can be prepared according to the method described in Reference example 32, etc. and potassium carbonate (2.0887 g; manufactured by Sigma-Aldrich Co.) were suspended in dehydrated DMF (10 mL; manufactured by Kanto Chemical Co., Inc.), added with sodium chlorodifluoroacetic acid (853 mg; manufactured by Tokyo Chemical Industry, Co., Ltd.), and stirred at 80° C. for 12 hours. The reaction solution was added to water and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=100:0→87:13) to obtain the title compound (264.7 mg).

Aufarbeitung

  1. washThe organic layer was washed twice with water and once with brine
  2. dry with materialdried over sodium sulfate
  3. customAfter the solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=100:0→87:13)

Quellen und Nachweise

ORD-Eintrag
ord-4cfb48990f0746ec86dce3827fff5c7c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304443B2

Notizen zur Reaktion

Wird geladen…