1,4-Dioxane → (S)-tert-butyl ((3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

HRID 1622559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622559
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:19]1[C:24](Br)=[CH:23][CH:22]=[CH:21][N:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O1CCOCC1.[CH2:33]([Sn](CCCC)(CCCC)C#CC)[CH2:34][CH2:35]C>CCOC(C)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:19]1[C:24]([C:33]#[C:34][CH3:35])=[CH:23][CH:22]=[CH:21][N:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 71164782(S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

Produkt 1

HCID 86687953(S)-tert-butyl ((3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a microwave vial containing (S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate (500 mg, 1.159 mmol) and a stir bar was added 1,4-dioxane (6 mL). To this solution was added tetrakis(triphenyl-phosphine)palladium(0) (67.0 mg, 0.058 mmol, 0.05 equiv.) and tributyl(prop-1-yn-1-yl)stannane (458 mg, 1.391 mmol, 1.2 equiv.). The vial was capped and irradiated in a microwave at 120° C. for 20 min. The vial was allowed to cool, diluted with hexanes (5 mL) and loaded directly to a normal phase silica gel column (80 g ISCO, 0 to 40% EtOAc in hexanes) to provide (S)-tert-butyl((3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate as a white solid.

Aufarbeitung

  1. customThe vial was capped
  2. customirradiated in a microwave at 120° C. for 20 min
  3. temperatureto cool

Quellen und Nachweise

ORD-Eintrag
ord-b48079aed11f43c0be5eadac36ed3480
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778941B2

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