Reaktion #163108

Reaktionsgleichung

2,6-dichloropyridine

[(1S)-1-(4-fluorophenyl)ethyl]amine

(biphenyl-2-ylmethylene)bis(dimethylphosphine)

sodium tert-butoxide

N2

→

title compound

Ausbeute 68.0%

6-Chloro-N-[(1S)-1-(4-fluorophenyl)ethyl]pyridin-2-amine

Ausbeute 68.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe flask was sealed
2. 2
   SonstigeThe solvent was removed
3. 3
   workup.ADDITIONEtOAc was added
4. 4
   Waschenthe mixture was washed with brine
5. 5
   Einengenwas concentrated

Vorschrift

To a 25 ml round bottom flask was added Pd(OAc)2 (45 mg, 0.2 mmol), (biphenyl-2-ylmethylene)bis(dimethylphosphine) (120 mg, 0.4 mmol) and sodium tert-butoxide (480 mg, 5.0 mmol). The flask was sealed and refilled with N2. To the mixture was added a solution of 2,6-dichloropyridine (300 mg, 2.0 mmol) and [(1S)-1-(4-fluorophenyl)ethyl]amine (306 mg, 2.2 mmol) in toluene (4 ml). The reaction mixture was heated at 85° C. overnight. The solvent was removed and EtOAc was added and the mixture was washed with brine and was concentrated. Flash chromatography (10-40% EtOAc in hexanes) gave the title compound (339 mg, 68%). 1H NMR (CDCl3) δ 1.55 (m, 3H), 4.66 (m, 1H), 5.07 (br s, 1H), 6.01 (m, 1H), 6.54 (m, 1H), 7.00 (m, 2H), 7.25 (m, 3H).

Quelle