Tetrafluoro-m-phenylenediamine dihydrochloride → 1-(9-Methyl-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indol-7-yl)-4-phenethylpyridin-2(1h)-one dihydrochloride

Participants

Reaction Steps

tert-Butyl 9-methyl-7-(2-oxo-4-phenethylpyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (1.2 g, 2.4 mmol) was deprotected and converted to the dihydrochloride salt according to the procedure of Example 30 (steps e and g) to provide the title compound (550 mg, 51%) as a yellow solid: mp 280-295° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.67 (s, 2H), 7.59-7.52 (m, 3H), 7.35-7.27 (m, 4H), 7.24-7.17 (m, 1H), 7.01 (dd, J=7.4, 2.0 Hz, 1H), 6.38-6.27 (m, 2H), 4.45 (s, 2H), 3.67 (s, 3H), 3.42 (t, J=6.4 Hz, 2H), 2.97-2.89 (m, 4H), 2.81-2.76 (m, 2H); ESI MS m/z 384 [M+H]; HPLC (Method B)>99% (AUC), tR=13.3 min.

Provenance & Evidence