tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(2-(1-methyl-6-((perfluorophenoxy)sulfonyl)-1H-indol-3-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Steps

The title compound was prepared in an analogous manner to that described in Intermediate E using perfluorophenyl 3-bromo-1-methyl-1H-indole-6-sulfonate and tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (INTERMEDIATE N) as the coupling partners to afford tert-butyl 4-(2-(1-methyl-6-((perfluorophenoxy)sulfonyl)-1H-indol-3-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate as an orange oily solid. m/z (ESI) 726.3 (M+Na)+. 1H NMR (400 MHz, DMSO-d6) δ ppm=8.26 (d, J=1.5 Hz, 1 H), 7.95 (s, 1 H), 7.77-7.73 (m, 1 H), 7.72 (d, J=8.5 Hz, 1 H), 7.66 (d, J=8.0 Hz, 1 H), 7.63 (d, J=1.9 Hz, 1 H), 7.59 (dd, J=1.8, 8.6 Hz, 1 H), 5.82 (br. s., 1 H), 3.99 (s, 3 H), 3.84 (br. s., 2 H), 3.10 (t, J=5.5 Hz, 2 H), 1.89 (br. s., 2 H), 1.38-1.29 (m, 9 H).

Provenance & Evidence