Reaktion #40412

Reaktionsgleichung

N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl]carboxamide

sodium borohydride

→

{4-[2-(aminomethyl)phenyl]phenyl)-N-(2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide

Ausbeute 43.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with ice cubes
2. 2
   workup.ADDITIONdiluted with DCM (100 mL)
3. 3
   Filtrationfiltered through celite
4. 4
   WaschenThe filtrate was washed with saturated aqueous NaHCO3
5. 5
   TrocknenThe organic layer was dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   WaschenHPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN

Vorschrift

A mixture of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl]carboxamide (200 mg, 0.442 mmol, 1.0 equiv.), cobalt chloride (86 mg, 0.664 mmol, 1.5 equiv.) and sodium borohydride (50 mg, 1.33 mmol, 3.0 equiv.) in DMF (15 mL) was stirred at 0° C. to rt for 3 days. The reaction was quenched with ice cubes, diluted with DCM (100 mL) and filtered through celite. The filtrate was washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, evaporated and HPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN gave {4-[2-(aminomethyl)phenyl]phenyl)-N-(2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (87 mg, 43%). MS found for C26H21ClN4O2 (M+H)+: 457.

Quelle