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

HRID 1181897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181897
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-05772d9a1e6f4ad7abb0a8504d0b87fc
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285666B2

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