Reaktion #1110050

Reaktionsgleichung

water

4-(5-bromo-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester

4-(5-Bromo-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Cs2CO3

potassium benzyltrifluoroborate

→

compound 29

Ausbeute 5.5%

5-Benzyl-6-(piperidin-4-yloxy)-isoquinoline

Ausbeute 5.5%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeArgon was bubbled through the mixture for 10 minutes
2. 2
   Temperaturthe reaction was heated
3. 3
   Temperaturto reflux for 16 h (incomplete conversion)
4. 4
   workup.ADDITIONwere added
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried over Na2SO4
7. 7
   SonstigeAfter removal of the solvents 2 mL 5-6 N HCl in isopropanol
8. 8
   workup.ADDITIONwas added
9. 9
   workup.DISTILLATIONAfter 2 h the solvents were distilled off

Vorschrift

0.3 mL of water were added to a solution of 81 mg (0.2 mmol) of 4-(5-bromo-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester (11), 195 mg (0.6 mmol) of Cs2CO3, 14.6 mg (0.02 mmol) of Pd(dppf)Cl2 and 51 mg (0.26 mmol) of potassium benzyltrifluoroborate in 3 mL of THF. Argon was bubbled through the mixture for 10 minutes and then the reaction was heated to reflux for 16 h (incomplete conversion). After cooling to room temperature water and ethyl acetate were added. The organic layer was separated, dried over Na2SO4. After removal of the solvents 2 mL 5-6 N HCl in isopropanol was added. After 2 h the solvents were distilled off and the remainder was subjected twice to preparative HPLC to give 3.5 mg compound 29 as trifluoroacetate.

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