(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid → 3-chloro-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)benzonitrile

HRID 130650

Reaktionsgleichung

Reaktionsgleichung von HRID 130650
[CH3:1][C:2]1([CH3:16])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11](B(O)O)=[CH:12][C:3]1=2.Br[C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:21]#[N:22]>[Pd]>[Cl:26][C:24]1[CH:23]=[C:20]([CH:19]=[C:18]([C:11]2[CH:10]=[CH:9][C:4]3[NH:5][C:6](=[O:8])[O:7][C:2]([CH3:16])([CH3:1])[C:3]=3[CH:12]=2)[CH:25]=1)[C:21]#[N:22]

Komponenten

4

Edukt 2

HCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acidHCID 159658933-Bromo-5-chlorobenzonitrile

Produkt 1

HCID 98798083-chloro-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-boronic acid (0.45 g, 2.04 mmol) was heated with 3-bromo-5-chlorobenzonitrile (0.42 g, 1.94 mmol) in the presence of soda ash (0.23 g, 2.17 mmol) and the 5% Pd/C catalyst in a solvent to produce 3-chloro-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)benzonitrile in good yields and purity. See, Table 2.

Quellen und Nachweise

ORD-Eintrag
ord-83019b3886f54b348723d2f7be12b4db
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381856B2

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