Binap, (A+-)- → 1-{4-[7-(2,6-Dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-phenyl}-cyclopropanecarbonitrile

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Reaction Steps

About 50 mg (0.2 mmol) of 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine and about 84 mg (0.38 mmol) of 1-(4-bromo-phenyl)-cyclopropanecarbonitrile were dissolved in about 10 ml of toluene. About 8 mg (0.009 mmol) of Pd(dba)3, about 17 mg (0.027 mmol) of BINAP, and about 50 mg (0.226 mmol) of 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 5 mg of 1-{4-[7-(2,6-dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-phenyl}-cyclopropanecarbonitrile (product having formula (X)) was isolated. ESI-MS: [M+H]+, 406.5; 1H NMR (DMSO-d6): δ 1.49 (q, 2 H, J=5.3 Hz), 1.72 (q, 2 H, J=5.3 Hz), 2.05 (s, 6 H), 2.67(s, 3 H), 7.18 (d, J=7.4 Hz, 2 H), 7.23 (m, 1H), 7.38 (d, J=6.85 Hz, 2 H), 7.63 (s, 1 H), 7.91 (s, 1 H), 8.06 (d, J=6.85 Hz, 2 H).

Provenance & Evidence