Hydrochloric Acid → 1-(2-Benzyloxy-5-bromo-benzyl)-5-Trifluoromethyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1053993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053993
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[NH:8][N:7]=1)=[O:5])[CH3:2].[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=1[CH2:30]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([F:13])([F:14])[F:12])[N:8]([CH2:30][C:24]2[CH:25]=[C:26]([Br:29])[CH:27]=[CH:28][C:23]=2[O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:7]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27269191H-Pyrazole-3-carboxylic acid, 5-(trifluoromethyl)-, ethyl esterHCID 117832201-(Benzyloxy)-4-bromo-2-(bromomethyl)benzene

Produkt 1

HCID 866856941-(2-Benzyloxy-5-bromo-benzyl)-5-Trifluoromethyl-1H-pyrazole-3-carboxylic acid ethyl esterAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-trifluoromethyl-1H-pyrazole-3-carboxylic acid ethyl ester (0.114 g, 0.55 mmol) and 1-benzyloxy-4-bromo-2-bromomethyl-benzene (0.196 g, 0.55 mmol) in DMF (2 ml) cooled at RT under N2 atmosphere was added K2CO3 (0.19 g, 1.375 mmol) The mixture was stirred at RT overnight, then acidified with HCl (2M, aq.) and extracted with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified by MPLC (10 g SiO2 cartridge, eluent 90% iso-hexane-10% EtOAc) yielding 0.18 g of title compound.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by MPLC (10 g SiO2 cartridge, eluent 90% iso-hexane-10% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-710dcf2459bf4c22b1131f8e708285ec
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394284B2

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