1-Methyl-3-(trifluoroacetyl)-1H-indole → 2,2,2-Trifluoro-1-[3-(4-fluorophenyl)imidazo[1,5-a]pyridin-7-yl]-1-(1-methyl-1H-indol-3-yl)ethanol

HRID 244471

Reaktionsgleichung

Reaktionsgleichung von HRID 244471
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][CH:10]=[C:4]2[CH:3]=1.C([Li])CCC.[F:23][C:24]([F:38])([F:37])[C:25]([C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH3:36])[CH:28]=1)=[O:26]>C1COCC1>[F:38][C:24]([F:23])([F:37])[C:25]([C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][CH:10]=[C:4]2[CH:3]=1)([C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH3:36])[CH:28]=1)[OH:26]

Komponenten

5

Edukt 3

HCID 35243881-Methyl-3-(trifluoroacetyl)-1H-indoleHCID 594372397-Bromo-3-(4-fluorophenyl)imidazo[1,5-a]pyridineHCID 178418339Butyllithium

Produkt 1

HCID 249598192,2,2-Trifluoro-1-[3-(4-fluorophenyl)imidazo[1,5-a]pyridin-7-yl]-1-(1-methyl-1H-indol-3-yl)ethanolAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a chilled (−78° C.) solution of 7-bromo-3-(4-fluorophenyl)imidazo[1,5-a]pyridine (58 mg, 0.2 mmol) in anhydrous THF (1 mL) was added n-butyllithium (0.1 mL of a 2.5 M solution in hexanes, 2.5 mmol). After 1 minute, a chilled (−78° C.) solution of 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethanone (68 mg, 0.3 mmol) in 1 mL of THF was added. After 5 minutes, the reaction mixture was quenched with 50 mL of brine solution and extracted with three 25 mL portions of methylene chloride. The combined organic extracts were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a yellow oil. The residue was purified by column chromatography over silica gel eluting with 0-70% ethyl acetate to afford 30 mg of the title compound as a light yellow solid. MS m/z 440 (MH+).

Aufarbeitung

  1. additionwas added
  2. waitAfter 5 minutes
  3. customthe reaction mixture was quenched with 50 mL of brine solution
  4. extractionextracted with three 25 mL portions of methylene chloride
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-70% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f76daba1af29439583acd6d6a77d06fb
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658637B2

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