Reaktion #360678

Reaktionsgleichung

7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine

1-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine

BINAP

KOt-Bu

→

[7-(2,6-dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Ausbeute 36.7%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude product was purified by preparative HPLC

Vorschrift

About 1 g (3.78 mmol) of 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine and about 2.04 g (7.56 mmol) of 1-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine were dissolved in about 500 ml of toluene. About 174 mg (0.19 mmol) of Pd(dba)3, about 340 mg (0.54 mmol) of BINAP, and about 500 mg (4.46 mmol) KOt-Bu were added to the solution. The mixture was kept at about 100° C. for about 24 hours under argon. The crude product was purified by preparative HPLC. About 90 mg of [7-(2,6-dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (product having formula (IX)) was isolated. Yield: about 5.2%. ESI-MS: [M+H]+, 454.6; 1H NMR (DMSO-d6): δ 1.90-2.05 (m, 10 H), 2.64(s, 3 H), 3.15 (m, 2 H), 3.59-3.64 (m, 4 H), 4.31 (t, J=5.2 Hz, 2 H), 7.09(d, J=9.2 Hz, 2 H), 7.18 (d, J=7.4 Hz, 2 H), 7.23 (m, 1 H), 7.60 (s, 1 H), 7.91 (s, 1 H), 7.98 (d, J=9.2 Hz, 2 H).

Quelle