Triacetoxyperiodinane → 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-formylphenyl)urea

HRID 1843047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1843047
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[C:20]([F:26])[CH:19]=3)=[O:16])=[CH:11][C:10]([C:27]([F:30])([F:29])[F:28])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[C:20]([F:26])[CH:19]=3)=[O:16])=[CH:11][C:10]([C:27]([F:30])([F:28])[F:29])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 708160761-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)urea

Produkt 1

HCID 715731471-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-formylphenyl)ureaAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)urea (240 mg, 0.54 mmol, 1.0 eq) in DCM (10 mL) and cooled to 0° C. was added Dess-Martin periodinane (345 mg, 0.813 mmol, 1.5 eq) slowly portion wise at 0° C. and stirred for 1 h at 0° C., and then stirred for 30 min. at RT. DCM was evaporated and EtOAC (50 mL) was added. The mixture was washed with water (20 mL), brine (20 mL), dried over anhydrous Na2SO4 and evaporated under vacuum. The crude product was purified by CC using EtOAc/PE (2:3) to yield compound 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-formylphenyl)urea (120 mg; 48%) as an yellow solid (TLC: EtOAc/PE (1:1); Rf: 0.5).

Aufarbeitung

  1. stirringstirred for 30 min. at RT
  2. customDCM was evaporated
  3. additionEtOAC (50 mL) was added
  4. washThe mixture was washed with water (20 mL), brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. customThe crude product was purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-e4f632db2b374d97aff3e85f7e26435a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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