Ethyl Acetate → 2-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo [1,5-a]pyridin-7-yl]-3,5-dimethylphenol

HRID 9220

Reaktionsgleichung

Reaktionsgleichung von HRID 9220
B(Br)(Br)Br.ClCCl.[CH:8]1([CH2:11][N:12]([CH2:34][CH:35]2[CH2:37][CH2:36]2)[C:13]2[C:14]([S:32][CH3:33])=[N:15][N:16]3[C:21]([C:22]4[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=4[O:30]C)=[CH:20][CH:19]=[CH:18][C:17]=23)[CH2:10][CH2:9]1.C(OCC)(=O)C>ClCCl>[CH:8]1([CH2:11][N:12]([CH2:34][CH:35]2[CH2:37][CH2:36]2)[C:13]2[C:14]([S:32][CH3:33])=[N:15][N:16]3[C:21]([C:22]4[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=4[OH:30])=[CH:20][CH:19]=[CH:18][C:17]=23)[CH2:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 21984670N,N-dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amineHCID 22277759Boron tribromide dichloromethane

Produkt 1

HCID 1357235202-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo [1,5-a]pyridin-7-yl]-3,5-dimethylphenolAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 1 M boron tribromide/dichloromethane solution (0.42 mL) was added to a solution of N,N-dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (35 mg) in dichloromethane (10 mL) at room temperature under a nitrogen atmosphere, and the mixture was stirred for 10 minutes. The reaction mixture was added to ice water, extraction was performed with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and the title compound (17 mg) was obtained from the n-hexane:ethyl acetate (6:1) fraction as white crystals.

Aufarbeitung

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7700df5685184235ac02c3c0c47a1faa
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091215B2

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