Reacción #61576

ord-f1eda020169d46eba1ae4e6f573ecd5a

Ecuación de reacción

O=C1NCCc2c(-c3ccccc3)[nH]c3cccc1c23
Compound 12
O=C1NCCc2c(-c3ccccc3)[nH]c3cccc1c23
2-Phenyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one
OB(O)c1ccc(C(F)(F)F)cc1
4-trifluoromethylphenylboronic acid
O=C1NCCc2c(-c3ccc(C(F)(F)F)cc3)[nH]c3cccc1c23
2-(4-trifluoromethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

In a manner analogous to the method described above for Compound 12, the tricyclic bromide (300 mg, 1.13 mmol) and 4-trifluoromethylphenylboronic acid (322 mg, 1.70 mmol) were coupled to yield 2-(4-trifluoromethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 261 mg (70%), as an off-white solid. mp 208-209° C.; 1H NMR (300 MHz, d6-DMSO) δ 3.09 (m, 2H), 3.40 (m, 2H), 7.27 (app t, 1H, J=7.8 Hz), 7.60 (dd, 1H, J=8.1, 0.9 Hz), 7.71 (dd, 1H, J=7.5, 0.6 Hz), 7.88 (m, 4H), 8.13 (br t, 1H), 11.77 (br s, 1H); MS (FAB, MH+) 331; Anal. (C18H13F3N2O.1.0 H2O) C, H, N.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07429578B2uspto-grants-2008_09