Reaktion #309872

Reaktionsgleichung

5-chloro-pyrazine-2-carboxylic acid methyl ester

Sodium hydride

3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol

3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol

→

title compound

5-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carboxylic acid methyl ester

Lösungsmittel

dimethyl formamide

dimethyl formamide

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe organic layer was washed with water, brine
2. 2
   Trocknendried over magnesium sulfate
3. 3
   FiltrationThe organic layer was filtered
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigethe resulting residue was purified by column chromatography
6. 6
   Wascheneluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (1:9:90)

Vorschrift

Sodium hydride (60% disp. in mineral oil, 332 mg, 8.3 mmol) was added to a stirred solution of 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (1.64 g, 7.5 mmol) in dimethyl formamide (4 ml). After 0.5 hours, a solution of 5-chloro-pyrazine-2-carboxylic acid methyl ester (1.95 g, 11.3 mmol) in dimethyl formamide (8 ml) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with dichloromethane and the organic layer was washed with water, brine and dried over magnesium sulfate. The organic layer was filtered, concentrated in vacuo and the resulting residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (1:9:90) to afford the title compound (E122). MS (ES+) m/e 354 [M+H]+.

Quelle