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5-bromo-1-(4-fluorophenyl)-1H-benzotriazole → 1-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]ethanol

HRID 244475
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 244475
Br[C:2]1[CH:17]=[CH:16][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[N:7]=[N:8][C:4]=2[CH:3]=1.C([Li])CCC.[CH3:23][C:24]1([CH3:45])[O:28][CH:27]([CH2:29][N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([C:39](=[O:44])[C:40]([F:43])([F:42])[F:41])=[CH:31]2)[CH2:26][O:25]1>C1COCC1>[CH3:23][C:24]1([CH3:45])[O:28][CH:27]([CH2:29][N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([C:39]([C:2]3[CH:17]=[CH:16][C:5]4[N:6]([C:9]5[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=5)[N:7]=[N:8][C:4]=4[CH:3]=3)([OH:44])[C:40]([F:43])([F:42])[F:41])=[CH:31]2)[CH2:26][O:25]1
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Komponenten

5

Edukt 3

HCID 594372265-bromo-1-(4-fluorophenyl)-1H-benzotriazoleHCID 594372891-[1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indol-3-yl]-2,2,2-trifluoroethanoneHCID 178418339Butyllithium

Produkt 1

HCID 594372331-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]ethanolAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-1H-benzotriazole (145 mg, 0.5 mmol) in anhydrous THF (3 mL) was added n-butyllithium (0.22 mL of a 2.5 M solution in hexanes, 0.55 mmol). After 1 minute, a chilled (−78° C.) solution of 1-[1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indol-3-yl]-2,2,2-trifluoroethanone (185 mg, 0.57 mmol) in 1 mL of THF was added. After 30 minutes, the mixture was quenched with brine solution (50 mL) and extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and solvent evaporated in vacuo to afford a yellow oil. The residue was purified by column chromatography over silica gel eluting with 0-60% ethyl acetate in hexanes and fractions corresponding to MS m/z 541 (MH+) peak were pooled and concentrated in vacuo to afford 150 mg of the title compound as a brownish solid.

Aufarbeitung

  1. additionwas added
  2. waitAfter 30 minutes
  3. customthe mixture was quenched with brine solution (50 mL)
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate, and solvent
  7. customevaporated in vacuo
  8. customto afford a yellow oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-60% ethyl acetate in hexanes and fractions corresponding to MS m/z 541 (MH+) peak
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d7a80266c1f64016a2a106d2eb53ce7c
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658637B2

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